Completing data — usually done within a minute
Basic information
- Standard SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3C(=C)C[C@@]21CC- InChIKey
RPLCPCMSCLEKRS-BPIQYHPVSA-N- Molecular formula
- C22H30O
- Average molar mass
- 310.481 g/mol
- Monoisotopic mass
- 310.22966558
Names & identifiers
- Preferred name
- Desogestrel
- IUPAC
- (1R,3aS,3bS,9aR,9bS,11aS)-11a-Ethyl-1-ethynyl-10-methylidene-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-ol
- English name
- Desogestrel
- Molecular formula
- C22H30O
- Molecular weight
- 310.47
Names & synonyms
Database identifiers
- CAS
54024-22-5- PubChem CID
- 40973
- DTXSID
DTXSID6022898- ChEMBL
CHEMBL1533- ChEBI
CHEBI:4453- UNII
- 81K9V7M3A3
- EC Number
- 258-929-4
- Nikkaji
- J12.635G
Properties
Physicochemical properties
- Melting point
- 109 · 109-110°C
- alpha
- 20 · D20 +55° (chloroform)
- Boiling point
- 390.62 °C · 390.62°C (rough estimate)
- Density
- 1.0169 · 1.0169 (rough estimate)
- refractive index
- 1.51 · 1.5100 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Practically insoluble in water, very soluble in methanol, freely soluble in anhydrous ethanol and in methylene chloride.
- pka
- 13.07 · 13.07±0.40(Predicted)
- form
- Solid
- color
- White to Almost white
- Merck
- 14 · 14,2926
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3
- InChIKey
- RPLCPCMSCLEKRS-UHFFFAOYSA-N
- SMILES
- C1C2C(CCC3C2C(=C)CC2(CC)C3CCC2(C#C)O)=CCC1
- FDA UNII
- 81 K9V7M3A3 · 81K9V7M3A3
- NCI Drug Dictionary
- Cerazette
- ATC code
- 3 AC09 · G03AC09
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 360 FD-H410 · H360FD-H410
- Precautionary statements
- 202 · P202-P273-P280-P308+P313-P391-P405
- Safety Statements
- 24 · 24/25
- RIDADR
- 3077 · UN 3077 9 / PGIII
- WGK Germany
- 3 · 3
- RTECS
- 7975000 · JF7975000
- HS Code
- 29372390 · 29372390
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Repr. 1B
- Hazardous Substances Data
- 54024 · 54024-22-5(Hazardous Substances Data)
Safety & regulation
Safety data
- wgk
- 3
- rtecs
- JF7975000
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29372390
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS09
- safety_code
- 24/25
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H360FD-H410
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Repr. 1B
- Precautionary statements
- P202-P273-P280-P308+P313-P391-P405
- Hazardous Substances Data
- 54024-22-5(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionDesogestrel is a synthetic progestogen. It inhibits ovulation and prevents fertilization in rabbits and mice. Desogestrel inhibits rhodamine 123 efflux, a measure of P-glycoprotein activity, ex vivo in human lymphocytes and CD8+ T cells in a dose-dependent manner. Formulations containing desogestrel have been used as oral contraceptives and for the treatment of polycystic ovary syndrome.
UsesA progestogen with low androgenic potency
General DescriptionDesogestrel, (17α)-13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol, is a 19-nortestosterone analog with good progestin activity. Likethe other progestins, it is orally active and used in combinationwith an estrogen in oral contraceptives. Desogestrel is aprodrug that must be oxidized to the 3-one in vivo to haveprogestational action. CYPs 2C9 and 2C19 have been implicatedin the initial hydroxylation of desogestrel at C3.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Desogestrel is a 17beta-hydroxy steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a progestin and a synthetic oral contraceptive.
Related reactions
Linked notes
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