Pregnanolone
Basic information
- CAS
128-20-1- Standard SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
AURFZBICLPNKBZ-YZRLXODZSA-N- Molecular formula
- C21H34O2
- Average molar mass
- 318.5 g/mol
- Monoisotopic mass
- 318.25588033
Overview
3alpha-hydroxy-5beta-pregnan-20-one is the 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one. It has a role as a sedative, an intravenous anaesthetic and a human metabolite. It is a 3alpha-hydroxy steroid and a 3-hydroxy-5beta-pregnan-20-one.
Names & identifiers
- Preferred name
- Pregnanolone
- IUPAC
- 1-[(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
- English name
- Eltanolone
- Molecular formula
- C21H34O2
- Molecular weight
- 318.49
Names & synonyms
PregnanoloneELTANOLONE128-20-13alpha-Hydroxy-5beta-pregnan-20-oneEltanolonaPregnan-3alpha-ol-20-oneEltanolonumDTXSID1046342Pregnan-20-one, 3-hydroxy-, (3alpha,5beta)-(3alpha,5beta)-3-hydroxypregnan-20-oneBXO86P3XXWKabi 2213
Show more names
5β-Pregnan-3α-ol-20-oneSKF 6455Kabi2213NSC 82867Pregnanolone IIEPIPREGNANOLONE
Kabi-2213SKF-6455NSC-82867Allopregnan-3 beta-ol-20-one1-[(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone3 Hydroxypregnan 20 onePregnan 3alpha ol 20 one3 alpha, 5 beta-Tetrahydroprogesterone
Database identifiers
- CAS
128-20-1- PubChem CID
- 31402
- DTXSID
DTXSID1046342- ChEMBL
CHEMBL210952- ChEBI
CHEBI:1712- UNII
- BXO86P3XXW
- EC Number
- 634-188-6
- Nikkaji
- J6.567F
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 500
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 149 °C · 149°C
- alpha
- 23 · D23 +59.6° (c = 0.3 in chloroform); D26 +108.5 ±1° (c = 9.23 mg/1.23 ml abs ethanol)
- Boiling point
- 397.64 °C · 397.64°C (rough estimate)
- Density
- 1.0234 · 1.0234 (rough estimate)
- refractive index
- 1.5344 · 1.5344 (estimate)
- storage temp.
- Store at RT
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
- pka
- 15.12 · 15.12±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- biological source
- synthetic (organic)
- Water Solubility
- 8 mg/L · 8mg/L(room temperature)
- 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
- InChIKey
- AURFZBICLPNKBZ-UHFFFAOYSA-N
- SMILES
- [H]C12CCC3C4CCC(C(C)=O)C4(C)CCC3C1(C)CC[C@H](O)C2
- FDA UNII
- 86 P3XXW · BXO86P3XXW
- NIST Chemistry Reference
- 3 Alpha-hydroxy-5beta-pregnan-20-one · 3Alpha-hydroxy-5beta-pregnan-20-one(128-20-1)
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 351 · H351
- Precautionary statements
- 281 · P281
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- Xn
- Risk Statements
- 40 · 40
- Safety Statements
- 22 · 22-36
- WGK Germany
- 3 · 3
- RTECS
- 4384000 · TU4384000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Carc. 2
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesCarc. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- TU4384000
- Toxicity
- LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)
- risk_code
- 40
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H351
- Hazard Classifications
- Carc. 2
- Precautionary statements
- P281
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.
Applications
UsesA hyponotic-anaesthetic agent.
Additional notes
DefinitionChEBI: The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.
Related reactions
6 records
Compound notes
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