Cyproterone acetate structure, CAS 427-51-0

Cyproterone acetate

CAS Number427-51-0

SynonymsCyprostat; Cyprosterone acetate; 6-Chloro-1b,2b-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-Acetate; Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1α,2α-methylene-, acetate; Cyproterone 17-O-acetate; Cyproteron acetate; SH 714; Cyproterone acetate; androcur; Cyproterone 17α-acetate; (1b,2b)-17-(Acetyloxy)-6-chloro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; cPA; Cyproteron-R acetate; CpA (VAN); Cyproterone (acetate)

Molecular FormulaC23H27ClO4

Molecular Weight416.94

Purity≥98%

Density1.3±0.1 g/cm3

Boiling Point525.9±50.0 °C at 760 mmHg

Melting Point200-201ºC

Flash Point

Appearancepowder

EINECS207-048-3

MSDSChineseEnglish

Symbol

Signal Word

Cat. No.: 2A-9009972 Purity: ≥98%
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Quality Control of [ 427-51-0 ] Purity: ≥98% SDS Specification MoL

Chemical & Physical Properties
CAS Number427-51-0
Catalog No.2A-9009972
Chinese Name醋酸环丙孕酮
SynonymsCyprostat; Cyprosterone acetate; 6-Chloro-1b,2b-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-Acetate; Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1α,2α-methylene-, acetate; Cyproterone 17-O-acetate; Cyproteron acetate; SH 714; Cyproterone acetate; androcur; Cyproterone 17α-acetate; (1b,2b)-17-(Acetyloxy)-6-chloro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; cPA; Cyproteron-R acetate; CpA (VAN); Cyproterone (acetate)
Molecular FormulaC23H27ClO4
Molecular Weight416.94
Purity≥98
Density1.3±0.1 g/cm3
Boiling Point525.9±50.0 °C at 760 mmHg
Melting Point200-201ºC
Appearancepowder
Water SolubilityPractically insoluble in water, very soluble in me
Storage Condition2-8°C
ApplicationCyproterone acetate is a highly active androgen receptor (AR) antagonist with an IC50 of 7.1 nM and a weak progesterone receptor agonist.
EINECS207-048-3
HTC2937290090
PubChem ID24278309
MDL NumberMFCD00864671
SMILES[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]34C
InChI1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1
InChI KeyUWFYSQMTEOIJJG-FDTZYFLXSA-N
NACRES CodeNA.77
UNSPSC41116107
MSDSmsds/9972_1_427_51_0.pdf
Use ofProperties Articles69 Name cyproterone acetate Synonym More Synonyms Cyproterone acetate Biological Activity Related Catalog Signaling Pathways >> Others >> Androgen Receptor Research Areas >> Endocrinology References [1]. Sonneveld, E., et al., Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays. Toxicol Sci, 2005. 83(1): p. 136-48. [2]. Attardi, B.J., S. Koduri, and S.A. Hild, Relative progestational and androgenic activity of four progestins used for male hormonal contraception assessed in vitro in relation to their ability to suppress LH secretion in the castrate male rat. Mol Cell End [3]. Arafa, N.M., Efficacy of echinacea on the action of cyproterone acetate in male rats. Pak J Biol Sci, 2010. 13(20): p. 966-76. Chemical & Physical Properties PSA 60.44000 Index of Refraction 1.582 InChIKey UWFYSQMTEOIJJG-FDTZYFLXSA-N Water Solubility Practically insoluble in water, very soluble in methylene chloride, freely soluble in acetone, soluble in methanol, sparingly soluble in anhydrous ethanol. Toxicological Information CHEMICAL IDENTIFICATION RTECS NUMBER : CHEMICAL NAME : 3'H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 6-chloro-1-beta,2-beta-dihydro- 17-hydroxy-, acetate CAS REGISTRY NUMBER : LAST UPDATED : DATA ITEMS CITED : MOLECULAR FORMULA : C24-H29-Cl-O4 MOLECULAR WEIGHT : WISWESSER LINE NOTATION : L F3 E6 D665 IV JU LUTJ A1 E1 RV1 RQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - man DOSE/DURATION : TOXIC EFFECTS : Liver - hepatitis (hepatocellular necrosis), zonal Liver - jaundice (or hyperbilirubinemia) hepatocellular Liver - liver function tests impaired TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Human - man DOSE/DURATION : TOXIC EFFECTS : Liver - hepatitis (hepatocellular necrosis), zonal Liver - hepatitis, fibrous (cirrhosis, post-necrotic scarring) Liver - liver function tests impaired TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - rat DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : 98570 ug/kg SEX/DURATION : male 4 week(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : male 14 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : male 16 week(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - impotence TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : male 56 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : male 16 week(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - other effects on male TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported 22286 ug/kg SEX/DURATION : male 52 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : female 16-19 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : female 11 day(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : female 1 day(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - other measures of fertility TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 17-20 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 16-19 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 7 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 7 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - other effects on male TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 35 day(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 18 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 17-20 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 13-22 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Effects on Newborn - delayed effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 10-22 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - delayed effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : male 28 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Parenteral SEX/DURATION : male 15 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Parenteral SEX/DURATION : female 7-21 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : SEX/DURATION : male 17 week(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : 7840 ug/kg SEX/DURATION : male 28 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported SEX/DURATION : female 17-20 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported SEX/DURATION : male 7 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Multiple routes SEX/DURATION : female 14-22 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 13-18 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - skin and skin appendages TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 5 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 12-17 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - respiratory system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 2 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 2 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - other measures of fertility TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 1-10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - other effects to embryo TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 10-15 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 10-15 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 12-14 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - skin and skin appendages TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 23-44 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : male 32 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 30 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : male 84 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : male 13 week(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 28 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 13-24 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : female 28-57 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - delayed effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 35 day(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 25 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 15-40 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SEX/DURATION : female 30-45 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - delayed effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 40 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 45 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SEX/DURATION : male 70 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct TYPE OF TEST : Micronucleus test TYPE OF TEST : Morphological transformation TYPE OF TEST : DNA damage TYPE OF TEST : Unscheduled DNA synthesis MUTATION DATA TEST SYSTEM : Rodent - mouse DOSE/DURATION : REFERENCE : FOBGA8 Folia Biologica (Krakow). (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.1- 1953- Volume(issue)/page/year: 27,263,1979 *** REVIEWS *** TOXICOLOGY REVIEW AEMBAP Advances in Experimental Medicine and Biology. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.1- 1967- Volume(issue)/page/year: 27,227,1972 TOXICOLOGY REVIEW RPHRA6 Recent Progress In Hormone Research. Proceedings of the Laurentian Hormone Conference. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1947- Volume(issue)/page/year: 26,337,1970 Safety Information GHS07, GHS08 Signal Word Warning Hazard Statements H312 + H332-H351 Precautionary Statements P261-P280 Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges Hazard Codes Xn:Harmful Safety Phrases S26-S36 RIDADR NONH for all modes of transport WGK Germany 3 RTECS GZ2230000 HS Code 2937290090
Transport InfoProduct name: Cyproterone acetate
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