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Chemistry

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Also known as: 57-83-0, Pregn-4-ene-3,20-dione, Agolutin, Luteohormone, Crinone, 4-pregnene-3,20-dione
Molecular Formula
C21H30O2
Molecular Weight
314.5  g/mol
InChI Key
RJKFOVLPORLFTN-LEKSSAKUSA-N
FDA UNII
4G7DS2Q64Y

Progesterone
The major progestational steroid that is secreted primarily by the CORPUS LUTEUM and the PLACENTA. Progesterone acts on the UTERUS, the MAMMARY GLANDS and the BRAIN. It is required in EMBRYO IMPLANTATION; PREGNANCY maintenance, and the development of mammary tissue for MILK production. Progesterone, converted from PREGNENOLONE, also serves as an intermediate in the biosynthesis of GONADAL STEROID HORMONES and adrenal CORTICOSTEROIDS.
Progesterone is a Progesterone.
1 2D Structure

Progesterone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C21H30O2/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/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
2.1.3 InChI Key
RJKFOVLPORLFTN-LEKSSAKUSA-N
2.1.4 Canonical SMILES
CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
2.1.5 Isomeric SMILES
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
2.2 Other Identifiers
2.2.1 UNII
4G7DS2Q64Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Pregnenedione

2. Progesterone, (13 Alpha,17 Alpha)-(+-)-isomer

3. Progesterone, (17 Alpha)-isomer

4. Progesterone, (9 Beta,10 Alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 57-83-0

2. Pregn-4-ene-3,20-dione

3. Agolutin

4. Luteohormone

5. Crinone

6. 4-pregnene-3,20-dione

7. Utrogestan

8. Corpus Luteum Hormone

9. Progestin

10. Prometrium

11. Syngesterone

12. Luteol

13. Glanducorpin

14. Pregnenedione

15. Progestasert

16. Progesterol

17. Progesteronum

18. Corlutin

19. Cyclogest

20. Gesterol

21. Gestone

22. Gestormone

23. Progestone

24. Progestron

25. Hormoflaveine

26. Methylpregnone

27. Progestronol

28. Corlutina

29. Corluvite

30. Corporin

31. Flavolutan

32. Fologenon

33. Gynlutin

34. Gynolutone

35. Hormoluton

36. Lingusorbs

37. Lucorteum

38. Luteodyn

39. Luteogan

40. Luteopur

41. Luteosan

42. Luteostab

43. Luteovis

44. Lutociclina

45. Lutocyclin

46. Lutocylin

47. Lutoform

48. Lutromone

49. Membrettes

50. Nalutron

51. Piaponon

52. Primolut

53. Progekan

54. Progestosol

55. Prolidon

56. Proluton

57. Protormone

58. Syngestrets

59. Syntolutan

60. Gestron

61. Lutidon

62. Lutogyl

63. Lutren

64. Prolets

65. Lutex

66. Luteal Hormone

67. Lucorteum Sol

68. Bio-luton

69. Lutocyclin M

70. Lipo-lutin

71. Luteocrin Normale

72. Luteinique

73. Prochieve

74. Prolutone

75. Lutin

76. 17alpha-progesterone

77. Synovex S

78. Projestaject

79. Gynoluton

80. Gesterol 50

81. Percutacrine Luteinique

82. Gesterol 100

83. Cyclogesterin

84. Akrolutin

85. Endometrin

86. Prolutin

87. Pregnene-3,20-dione

88. (s)-progesterone

89. Colprosterone

90. Progesteron

91. Progestogel

92. Progeston

93. 3,20-pregnene-4

94. Gelbkoerperhormon

95. Crinone Progesterone Gel

96. Gestiron

97. Lugesteron

98. Progestol

99. Luteol (van)

100. Lutocuclin M

101. Nsc-9704

102. .beta.-progesterone

103. Percutacrine

104. (s)-4-pregnene-3,20-dione

105. Progeffik

106. Utrogest

107. Vitarrine

108. Luteum

109. Progesteronum [inn-latin]

110. Delta(4)-pregnene-3,20-dione

111. Progesterona [inn-spanish]

112. (s)-pregn-4-en-3,20-dione

113. Delta(sup 4)-pregnene-3,20-dione

114. Ccris 533

115. Prontogest

116. Estima

117. 17.alpha.-progesterone

118. Hsdb 3389

119. Progesterone [progestins]

120. Ai3-51682

121. Prometrium (tn)

122. Pregn-4-en-3,20-dione

123. Crinone (tn)

124. 6alpha-methylpregn-4-en-17alpha-ol-3,20-dione

125. Chebi:17026

126. .delta.4-pregnene-3,20-dione

127. 17alpha-hydroxy-6alpha-methylpregn-4-ene-3,20-dione

128. Progesterone, Micronized

129. Pregn-4-ene-3,20-dione, 17alpha-hydroxy-6alpha-methyl-

130. Component Of Cyclogesterin

131. Nsc-64377

132. 4-pregnen-3,20-dione

133. .delta.(sup4)-pregnene-3,20-dione

134. Chembl103

135. D4-pregnene-3,20-dione

136. Mls000028517

137. 4g7ds2q64y

138. (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

139. Nsc9704

140. U 3672

141. Nsc64377

142. Ncgc00015785-04

143. Smr000058345

144. Dsstox_cid_2370

145. Dsstox_rid_76562

146. Dsstox_gsid_22370

147. (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3h-cyclopenta[a]phenanthren-3-one

148. 6.alpha.-methylpregn-4-en-17.alpha.-ol-3,20-dione

149. 17.alpha.-hydroxy-6.alpha.-methylpregn-4-ene-3,20-dione

150. Progesterona

151. Progestan

152. Pregn-4-ene-3,20-dione, 17.alpha.-hydroxy-6.alpha.-methyl-

153. (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

154. Smr000653542

155. Progesterone (prometrium)

156. Wln: L E5 B666 Ov Mutj A1 E1 Fv1

157. Sr-01000000088

158. Sr-01000076054

159. Nsc 9704

160. Einecs 200-350-6

161. Nsc 64377

162. Pregn-4-ene-3, 17.alpha.-hydroxy-6.alpha.-methyl-

163. Bhr-100

164. Unii-4g7ds2q64y

165. Duraprogen

166. Progestrel

167. Lipolutin

168. Lutinus

169. Lutogynon

170. Progesterone??

171. Beta-progesterone

172. 1dbb

173. 17a-progesterone

174. Cas-57-83-0

175. Delta(sup4)-pregnene-3,20-dione

176. Progesterone [usp:inn:ban:jan]

177. Racemic Progesterone

178. Prestwick_411

179. Mfcd00003658

180. Cidr

181. Milprosa

182. Mpp22

183. 2aa6

184. 4bb2

185. Opera_id_292

186. Progesterone, >=99%

187. Prestwick0_000477

188. Prestwick1_000477

189. Prestwick2_000477

190. Prestwick3_000477

191. Spectrum5_002053

192. Progesterone [mi]

193. Cyclogesterin (salt/mix)

194. Progesterone [inn]

195. Progesterone [jan]

196. Bmse000482

197. Epitope Id:116051

198. Ec 200-350-6

199. Progesterone [hsdb]

200. Progesterone [inci]

201. Pregn-4-ne-3,20-ione

202. Schembl7671

203. Progesterone [vandf]

204. Bidd:pxr0094

205. Lopac0_000895

206. Bspbio_000614

207. Progesterone [mart.]

208. Mls000758277

209. Mls001074187

210. Mls001423982

211. Mls002222367

212. Bidd:er0547

213. P0130_sigma

214. Progesterone [usp-rs]

215. Progesterone [who-dd]

216. Progesterone [who-ip]

217. Spbio_002553

218. .delta.-pregnene-3,20-dione

219. Bdbm8903

220. Bpbio1_000676

221. Gtpl2377

222. Hydroxyprogesterone Caproic Acid

223. Dtxsid3022370

224. Progesterone (jp17/usp/inn)

225. Bhr-310

226. Eti-411

227. Progesterone [green Book]

228. 1a28

229. 1h60

230. Hms1569o16

231. Hms2051o05

232. Hms2090j07

233. Hms2096o16

234. Hms2230f23

235. Hms2233p11

236. Hms3262d12

237. Hms3713o16

238. Pregnene, 3,20-dione-delta^4-

239. Progesterone [orange Book]

240. Progesterone [ep Monograph]

241. Bcp22000

242. Bijuva Component Progesterone

243. Hy-n0437

244. Zinc4428529

245. Progesterone [usp Monograph]

246. Tox21_113157

247. Tox21_201792

248. Tox21_300307

249. Tox21_500895

250. Ac-700

251. Cmc_13406

252. Lmst02030159

253. Progesteronum [who-ip Latin]

254. S1705

255. Akos015894908

256. Progesterone; 4-pregnene-3,20-dione

257. Ccg-100766

258. Cs-1937

259. Db00396

260. Dr-2011

261. Fd12045

262. Lp00895

263. Nc00016

264. Progesterone Component Of Bijuva

265. Sdccgsbi-0050870.p002

266. Progesterone 1.0 Mg/ml In Acetonitrile

267. Progesterone 100 Microg/ml In Methanol

268. Ncgc00022185-03

269. Ncgc00022185-04

270. Ncgc00022185-05

271. Ncgc00022185-06

272. Ncgc00022185-07

273. Ncgc00022185-08

274. Ncgc00022185-09

275. Ncgc00022185-10

276. Ncgc00022185-11

277. Ncgc00022185-12

278. Ncgc00022185-14

279. Ncgc00022185-21

280. Ncgc00090798-01

281. Ncgc00090798-02

282. Ncgc00254120-01

283. Ncgc00259341-01

284. Ncgc00261580-01

285. (1s,10s,11s,14s,15s,2r)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0<2,7>.0 <11,15>]heptadec-6-ene

286. As-12660

287. Cpd000058345

288. Nci60_042166

289. Progesterone 1000 Microg/ml In Methanol

290. Fe-999913

291. Eu-0100895

292. P0478

293. (14beta,17alpha)-pregn-4-ene-3,20-dione

294. Progesterone, Meets Usp Testing Specifications

295. Progesterone, Vetec(tm) Reagent Grade, 98%

296. C00410

297. D00066

298. P 0130

299. Q26963

300. S00293

301. Progesterone, Vetranal(tm), Analytical Standard

302. Q-201624

303. Sr-01000000088-5

304. Sr-01000000088-6

305. Sr-01000076054-1

306. Sr-01000076054-4

307. Brd-k64994968-001-03-6

308. 32104fb6-bf81-4f6e-83c2-024deeaeb272

309. Progesterone, British Pharmacopoeia (bp) Reference Standard

310. Progesterone, Powder, Bioreagent, Suitable For Cell Culture

311. Progesterone, European Pharmacopoeia (ep) Reference Standard

312. Progesterone, Gamma-irradiated, Bioxtra, Suitable For Cell Culture

313. Progesterone, United States Pharmacopeia (usp) Reference Standard

314. Progesterone-water Soluble, Powder, Bioreagent, Suitable For Cell Culture

315. Progesterone For Peak Identification, European Pharmacopoeia (ep) Reference Standard

316. Progesterone For System Suitability, European Pharmacopoeia (ep) Reference Standard

317. Progesterone, Pharmaceutical Secondary Standard; Certified Reference Material

318. (1s,2r,10s,11s,14s,15s)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-en-5-one

319. 137940-28-4

320. 753497-20-0

321. Progesterone Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 314.5 g/mol
Molecular Formula C21H30O2
XLogP33.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass314.224580195 g/mol
Monoisotopic Mass314.224580195 g/mol
Topological Polar Surface Area34.1 Ų
Heavy Atom Count23
Formal Charge0
Complexity589
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameCrinone
PubMed HealthProgesterone
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Active IngredientProgesterone
Dosage FormGel
Routevaginal; Vaginal
Strength8%; 4%
Market StatusPrescription
CompanyWatson Labs; Columbia Res Labs

2 of 8  
Drug NameEndometrin
PubMed HealthProgesterone
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Drug LabelEndometrin (progesterone) Vaginal Insert contains micronized progesterone. Endometrin is supplied with polyethylene vaginal applicators.The active ingredient, progesterone, is present in 100 mg amount along with other excipients. The chemical name fo...
Active IngredientProgesterone
Dosage FormInsert
RouteVaginal
Strength100mg
Market StatusPrescription
CompanyFerring

3 of 8  
Drug NameProgesterone
PubMed HealthProgesterone
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Drug LabelPROMETRIUM (progesterone, USP) Capsules contain micronized progesterone for oral administration. Progesterone has a molecular weight of 314.47 and a molecular formula of C21H30O2. Progesterone (pregn-4-ene-3, 20-dione) is a white or creamy white, odo...
Active IngredientProgesterone
Dosage FormCapsule; Injectable
RouteInjection; Oral
Strength200mg; 50mg/ml; 100mg
Market StatusPrescription
CompanySofgen Pharms; Hikma Farmaceutica; Watson Labs (utah); Banner Pharmacaps; Teva Pharms; Fresenius Kabi Usa; Luitpold

4 of 8  
Drug NamePrometrium
PubMed HealthProgesterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Drug LabelPROMETRIUM (progesterone, USP) Capsules contain micronized progesterone for oral administration. Progesterone has a molecular weight of 314.47 and a molecular formula of C21H30O2. Progesterone (pregn-4-ene-3, 20-dione) is a white or creamy white, odo...
Active IngredientProgesterone
Dosage FormCapsule
Routeoral; Oral
Strength200mg; 300mg; 100mg
Market StatusPrescription
CompanyAbbvie

5 of 8  
Drug NameCrinone
PubMed HealthProgesterone
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Active IngredientProgesterone
Dosage FormGel
Routevaginal; Vaginal
Strength8%; 4%
Market StatusPrescription
CompanyWatson Labs; Columbia Res Labs

6 of 8  
Drug NameEndometrin
PubMed HealthProgesterone
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Drug LabelEndometrin (progesterone) Vaginal Insert contains micronized progesterone. Endometrin is supplied with polyethylene vaginal applicators.The active ingredient, progesterone, is present in 100 mg amount along with other excipients. The chemical name fo...
Active IngredientProgesterone
Dosage FormInsert
RouteVaginal
Strength100mg
Market StatusPrescription
CompanyFerring

7 of 8  
Drug NameProgesterone
PubMed HealthProgesterone
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Drug LabelPROMETRIUM (progesterone, USP) Capsules contain micronized progesterone for oral administration. Progesterone has a molecular weight of 314.47 and a molecular formula of C21H30O2. Progesterone (pregn-4-ene-3, 20-dione) is a white or creamy white, odo...
Active IngredientProgesterone
Dosage FormCapsule; Injectable
RouteInjection; Oral
Strength200mg; 50mg/ml; 100mg
Market StatusPrescription
CompanySofgen Pharms; Hikma Farmaceutica; Watson Labs (utah); Banner Pharmacaps; Teva Pharms; Fresenius Kabi Usa; Luitpold

8 of 8  
Drug NamePrometrium
PubMed HealthProgesterone (By mouth)
Drug ClassesEndocrine-Metabolic Agent, Endometrial Hyperplasia Agent, Female Reproductive Agent
Drug LabelPROMETRIUM (progesterone, USP) Capsules contain micronized progesterone for oral administration. Progesterone has a molecular weight of 314.47 and a molecular formula of C21H30O2. Progesterone (pregn-4-ene-3, 20-dione) is a white or creamy white, odo...
Active IngredientProgesterone
Dosage FormCapsule
Routeoral; Oral
Strength200mg; 300mg; 100mg
Market StatusPrescription
CompanyAbbvie

4.2 Therapeutic Uses

Progestins

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Prochieve 4% is indicated for the treatment of secondary amenorrhea. Prochieve 8% is indicated for use in women who have failed to respond to treatment with Prochieve 4%. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for PROCHIEVE (progesterone) gel (November 2009). Available from, as of March 1, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=13486


Prochieve 8% is indicated for progesterone supplementation or replacement as part of an Assisted Reproductive Technology ("ART") treatment for infertile women with progesterone deficiency. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for PROCHIEVE (progesterone) gel (November 2009). Available from, as of March 1, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=13486


Progesterone is used orally or intravaginally for the management of secondary amenorrhea.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3279


For more Therapeutic Uses (Complete) data for PROGESTERONE (9 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNING: CARDIOVASCULAR DISORDERS, BREAST CANCER and PROBABLE DEMENTIA FOR ESTROGEN PLUS PROGESTIN THERAPY. Cardiovascular Disorders and Probable Dementia: Estrogens plus progestin therapy should not be used for the prevention of cardiovascular disease or dementia. The Women's Health Initiative (WHI) estrogen plus progestin substudy reported increased risks of deep vein thrombosis, pulmonary embolism, stroke and myocardial infarction in postmenopausal women (50 to 79 years of age) during 5.6 years of treatment with daily oral conjugated estrogens (CE) (0.625 mg) combined with medroxyprogesterone acetate (MPA) (2.5 mg), relative to placebo. The WHI Memory Study (WHIMS) estrogen plus progestin ancillary study of the WHI reported an increased risk of developing probable dementia in postmenopausal women 65 years of age or older during 4 years of treatment with daily CE (0.625 mg) combined with MPA (2.5 mg), relative to placebo. It is unknown whether this finding applies to younger postmenopausal women. Breast Cancer: The WHI estrogen plus progestin substudy also demonstrated an increased risk of invasive breast cancer. In the absence of comparable data, these risks should be assumed to be similar for other doses of CE and MPA, and other combinations and dosage forms of estrogens and progestins. Progestins with estrogens should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.

US Natl Inst Health; DailyMed. Current Medication Information for Prometrium (progesterone) capsule (Updated September 2013). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0224b5a6-25a3-44c9-b94f-90e2e064c164


Other doses of oral conjugated estrogens with medroxyprogesterone and other combinations and dosage forms of estrogens and progestins were not studied in the WHI clinical trials. In the absence of comparable data and product-specific studies, the relevance of the WHI findings to other products has not been established. Therefore, the risks should be assumed to be similar for all estrogen and progestin products. Because of these risks, estrogens with or without progestins should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.

US Natl Inst Health; DailyMed. Current Medication Information for Prometrium (progesterone) capsule (March 2008). Available from, as of February 23, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=6971


Adverse effects reported in patients receiving oral progesterone include dizziness, breast pain, headache, abdominal pain, fatigue, viral infection, abdominal distention, musculoskeletal pain, emotional lability, irritability, and upper respiratory tract infection. Extreme dizziness and/or drowsiness, blurred vision, slurred speech, difficulty walking, loss of consciousness, vertigo, confusion, disorientation, and shortness of breath have been reported in a few women receiving the drug. Hypotension and syncope have occurred rarely in women receiving progesterone capsules.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3279


Adverse effects reported in patients receiving progesterone vaginal gel include breast pain/enlargement, somnolence, constipation, nausea, headache, and perineal pain.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3279


For more Drug Warnings (Complete) data for PROGESTERONE (19 total), please visit the HSDB record page.


4.4 Drug Indication

**Gelatinized capsules** The gelatinized capsules are indicated for use in the prevention of endometrial hyperplasia in non-hysterectomized postmenopausal women who are receiving conjugated estrogens tablets. They are also indicated for use in secondary amenorrhea. **Vaginal gel** Progesterone gel (8%) is indicated as progesterone supplementation or replacement as part of an Assisted Reproductive Technology (ART) treatment for infertile women with progesterone deficiency. The lower concentration progesterone gel (4%) is used in the treatment of secondary amenorrhea, with the use of the 8% concentration if there is no therapeutic response to the 4% gel. **Vaginal insert** This form is indicated to support embryo implantation and early pregnan