CAS Number516-54-1
Synonymspregnanalone; PREGNAN-3A-OL-20-ONE; (+)-3α-Hydroxy-5α-pregnan-20-one; (3α)-3-Hydroxypregnan-20-one; Butabindide oxalate; 3α,5α-THP; (3α)-Allopregnanolone; 5-Pregnan-3-ol-20-one; 3alpha-hydroxy-5alpha-pregnan-20-one; MFCD00003677; UNII:S39XZ5QV8Y; Pregnanolone II; 3alpha-hydroxy-5beta-pregnan-20-one; ALLOPREGNAN-3ALPHA-OL-20-ONE; Brexanolone; Allopregnanolone; 3α-Hydroxy-5α-pregnan-20-one; 3a-Hydroxy-5a-pregnane-20-one; (3α,5α)-3-Hydroxypregnan-20-one; 3a-Hydroxy-5a-pregnan-20-one; (+)-3a-Hydroxy-5a-pregnan-20-one; 3α,5α-Tetrahydroprogesterone; 5α-Pregnan-3α-ol-20-one; 5alpha-Pregnan-3alpha-ol-20-one; LJPC-0712
Molecular FormulaC21H34O2
Molecular Weight323.52
Purity≥98 (CP)%
Density1.1±0.1 g/cm3
Boiling Point431.2±18.0 °C at 760 mmHg
Melting Point176-178°
Appearancesolution
EINECS200-659-6
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 516-54-1 |
| Catalog No. | 2A-9009112 |
| Chinese Name | 5alpha-孕甾-3alpha-醇-20-酮 |
| Synonyms | pregnanalone; PREGNAN-3A-OL-20-ONE; (+)-3α-Hydroxy-5α-pregnan-20-one; (3α)-3-Hydroxypregnan-20-one; Butabindide oxalate; 3α,5α-THP; (3α)-Allopregnanolone; 5-Pregnan-3-ol-20-one; 3alpha-hydroxy-5alpha-pregnan-20-one; MFCD00003677; UNII:S39XZ5QV8Y; Pregnanolone II; 3alpha-hydroxy-5beta-pregnan-20-one; ALLOPREGNAN-3ALPHA-OL-20-ONE; Brexanolone; Allopregnanolone; 3α-Hydroxy-5α-pregnan-20-one; 3a-Hydroxy-5a-pregnane-20-one; (3α,5α)-3-Hydroxypregnan-20-one; 3a-Hydroxy-5a-pregnan-20-one; (+)-3a-Hydroxy-5a-pregnan-20-one; 3α,5α-Tetrahydroprogesterone; 5α-Pregnan-3α-ol-20-one; 5alpha-Pregnan-3alpha-ol-20-one; LJPC-0712 |
| Molecular Formula | C21H34O2 |
| Molecular Weight | 323.52 |
| Purity | ≥98 (CP) |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 431.2±18.0 °C at 760 mmHg |
| Melting Point | 176-178° |
| Appearance | solution |
| Water Solubility | chloroform: 20 mg/mL, clear, colorless |
| Storage Condition | Store at RT |
| Application | Allopregnanolone is a progesterone metabolite. It is an allosteric modulator of GABA receptors. |
| EINECS | 200-659-6 |
| PubChem ID | 329769193 |
| SMILES | C[C@@]12[C@](CCC3C2CC[C@@]4(C)C3CCC4C(C)=O)([H])C([2H])([2H])[C@@](O)([2H])C([2H])([2H])C1 |
| InChI | 1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16?,17?,18?,19?,20-,21+/m0/s1/i8D2,12D2,15D |
| InChI Key | AURFZBICLPNKBZ-DXLOLUHISA-N |
| NACRES Code | NA.12 |
| UNSPSC | 12352211 |
| Hazard Symbols | Transport |
| MSDS | msds/9112_1_516_54_1.pdf |
| Bioactivity | Allopregnanolone is a progesterone metabolite. Allopregnanolone is an allosteric modulator of the GABA receptor. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor Signaling Pathways >> Neuronal Signaling >> GABA Receptor Natural Products >> Steroids Research Areas >> Neurological Disease Target Human Endogenous Metabolite In Vitro Allopregnanolone induces a significant increase in proliferation of neuroprogenitor cells derived from the rat hippocampus and human neural stem cells derived from the cerebral cortex in a dose-dependent manner. Allopregnanolone increases the expression of genes that promote mitosis and inhibits the expression of genes that repress cell proliferation[1]. Its biosynthesis begins with progesterone, which is converted to dihydroprogesterone by the enzyme 5α-DHP and after that, the enzyme 3α-HSOR catalyses the reduction of dihydroprogesterone toward allopregnanolone[2] In Vivo Allopregnanolone increases both the K+-evoked [3H]-glutamate and [3H]-GABA release in P rats. The neurosteroid also increases the basal release of [3H]-glutamate in VO rats in an effect that is dependent on the modulation of NMDA receptors as is reverted by Mg2+[2]. At therapeutic doses by either subcutaneous or intravenous routes, allopregnanolone mouse plasma levels range between 34-51ng/mL by 30min[3]. Allopregnanolone-induced neurogenesis correlates with restoration of learning and memory function in a mouse model of Alzheimer's disease and is comparably efficacious in aged normal mice[4]. Progesterone and allopregnanolone has shown neuroprotective effects in different experimental models including stroke and spinal cord injury[5]. Animal Admin Rats: Allopregnanolone is dissolved in propylenglycol to a concentration of 0.6 mM and diluted in Krebs Ringer bicarbonate glucose (KRBG) Mg2+-free buffer at pH 7.4 to 120 nM. To antagonize GABA receptors, 120 nM allopregnanolone plus 9.8 μM Bic (Bic+Allo groups) or 9.8 μM Bic alone (Bic groups) is used[2]. Mice: Allopregnanolone is dissolved in 20%w/v HBCD solution at 2.5 mg/mL by brief sonication and is subcutaneously (SC) injected to mice at 0.5, 1, and 10 mg/kg. Additionally, allopregnanolone is dissolved in 6%w/v SBECD solution at 0.5 mg/mL and injected IV to mice at 0.1, 0.5, and 1 mg/kg. HBCD or SBECD alone are included as vehicle controls. Topical transdermal is applied on the shaved dorsal surface at 50mg/kg using a gel solution of 3.3% allopregnanolone (w/w), 45% DMSO, 30% EtOH, 2.5% Klucel MF, 19.2% PEG-300. Intranasal formulations are prepared in both 100% castor oil and 20% HBCD. Intramuscular formulation is administered to mice as allopregnanolone 1.5 mg/mL in 6% SBECD[3]. References [1]. Wang JM, et al. The neurosteroid allopregnanolone promotes proliferation of rodent and human neural progenitor cells and regulates cell-cycle gene and protein expression. J Neurosci. 2005 May 11;25(19):4706-18. [2]. Giuliani FA, et al. Allopregnanolone and puberty: modulatory effect on glutamate and GABA release and expression of 3α-hydroxysteroid oxidoreductase in the hypothalamus of female rats. Neuroscience. 2013 Jul 23;243:64-75. [3]. Irwin RW, et al. Allopregnanolone Preclinical Acute Pharmacokinetic and Pharmacodynamic Studies to Predict Tolerability and Efficacy for Alzheimer's Disease. PLoS One. 2015 Jun 3;10(6):e0128313. [4]. Irwin RW, et al. Allopregnanolone as regenerative therapeutic for Alzheimer's disease: translational development and clinical promise. Prog Neurobiol. 2014 Feb;113:40-55. [5]. Guennoun R, et al. Progesterone and allopregnanolone in the central nervous system: response to injury and implication for neuroprotection. J Steroid Biochem Mol Biol. 2015 Feb;146:48-61. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 431.2±18.0 °C at 760 mmHg Melting Point 176-178° Molecular Formula C21H34O2 Molecular Weight 318.493 Flash Point 183.9±13.8 °C Exact Mass 318.255890 PSA 37.30000 LogP 4.89 Appearance of Characters White solid Vapour Pressure 0.0±2.3 mmHg at 25°C Index of Refraction 1.524 InChIKey AURFZBICLPNKBZ-SYBPFIFISA-N SMILES CC(=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C Storage condition Store at RT Water Solubility chloroform: 20 mg/mL, clear, colorless |
| Use of | Allopregnanolone is a progesterone metabolite. Allopregnanolone is an allosteric modulator of the GABA receptor. Properties Articles69 Name 3α-hydroxy-5α-pregnan-20-one Synonym More Synonyms 5alpha-Pregnan-3alpha-ol-20-one Biological Activity Description Allopregnanolone is a progesterone metabolite. Allopregnanolone is an allosteric modulator of the GABA receptor. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor Signaling Pathways >> Neuronal Signaling >> GABA Receptor Natural Products >> Steroids Research Areas >> Neurological Disease Human Endogenous Metabolite In Vitro Allopregnanolone induces a significant increase in proliferation of neuroprogenitor cells derived from the rat hippocampus and human neural stem cells derived from the cerebral cortex in a dose-dependent manner. Allopregnanolone increases the expression of genes that promote mitosis and inhibits the expression of genes that repress cell proliferation[1]. Its biosynthesis begins with progesterone, which is converted to dihydroprogesterone by the enzyme 5α-DHP and after that, the enzyme 3α-HSOR catalyses the reduction of dihydroprogesterone toward allopregnanolone[2] References [1]. Wang JM, et al. The neurosteroid allopregnanolone promotes proliferation of rodent and human neural progenitor cells and regulates cell-cycle gene and protein expression. J Neurosci. 2005 May 11;25(19):4706-18. [2]. Giuliani FA, et al. Allopregnanolone and puberty: modulatory effect on glutamate and GABA release and expression of 3α-hydroxysteroid oxidoreductase in the hypothalamus of female rats. Neuroscience. 2013 Jul 23;243:64-75. [3]. Irwin RW, et al. Allopregnanolone Preclinical Acute Pharmacokinetic and Pharmacodynamic Studies to Predict Tolerability and Efficacy for Alzheimer's Disease. PLoS One. 2015 Jun 3;10(6):e0128313. [4]. Irwin RW, et al. Allopregnanolone as regenerative therapeutic for Alzheimer's disease: translational development and clinical promise. Prog Neurobiol. 2014 Feb;113:40-55. [5]. Guennoun R, et al. Progesterone and allopregnanolone in the central nervous system: response to injury and implication for neuroprotection. J Steroid Biochem Mol Biol. 2015 Feb;146:48-61. Chemical & Physical Properties Molecular Formula C21H34O2 Exact Mass 318.255890 PSA 37.30000 Appearance of Characters White solid Index of Refraction 1.524 InChIKey AURFZBICLPNKBZ-SYBPFIFISA-N Storage condition Store at RT |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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