(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 485
• Molecular Formular: C22H32O3
• Molecular Mass: 344.48768
• Monoisotopic Mass: 344.23514488
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)[C@H](C3)C)C)CC2)CC1)C)C(=O)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
• InChIKey: FRQMUZJSZHZSGN-HBNHAYAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: medroxyprogesterone
• Brand Name: Aragest; Aragest 5; Asconale; Clinofem; Clinovir; Colirest; DMPA; Depo-Clinovir; Depo-Prodasone; Depo-Progestin; Depo-Promone; Depot-Medroxyprogesterone acetate; Farlutal; Farlutin; G-Farlutal; Gestapuran; Hematrol; Hysron; Indivina; Lunelle; Lutopolar; Lutoral; Med-Pro; Meprate; Metigestrona; MPA Gyn 5; Nadigest; Nidaxin; Novo-Medrone; Oragest; Perlutex; Perlutex Leo; Prodasone; Progestalfa; Progevera; Proverone; Ralovera; Repromap; Repromix; Sirprogen; Sodelut G; Veramix; Provera
• Synonyms: Medroxyprogesteronum [INN-Latin]; Medroxyprogesteron acetate; Medroxyprogesteron; Medroxiprogesteronum; Medroxiprogesterona [INN-Spanish]; Medrossiprogesterone [Dcit]; Medroprogesterone Acetate; MAP; Hydroxymethylprogesterone; CBP-1011; Medroxyprogesterone; 6α-17-Hydroxy-6-(methyl-d3)-pregn-4-ene-3,20-dione; 17α-Hydroxy-6α-methyl-progesterone; 17-Hydroxy-6α-methylpregn-4-ene-3,20-dione; NSC 27408; Medroxy Progesterone; 17α-Hydroxy-6α-methyl-4-pregnene-3,20-dione; 17α-Hydroxy-6α-methylprogesterone; 6α-Methyl-5-pregnen-17α-ol-3,20-dione; 6-Dihydromegestrol; Medroxyprogesterone; 17α-羟基-6α-甲基-4-孕烯-3,20-二酮; 17α-羟基-6α-甲基孕酮; 6α-甲基-5-孕甾烯-17α-醇-3,20-二酮; 6-二氢甲地孕酮; 甲羟孕酮

Database IDs

• CAS Number: 520-85-4
• EC Number: 208-298-6
• MDL Number: MFCD00069474
• Beilstein Number: 2510965
• PubChem SID: 24870138; 24897065; 46508895; 160963948
• PubChem CID: 10631; 1063110631
• Chemspider ID: 10185
• Wikipedia Title: Medroxyprogesterone

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.699646
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6881983
• LogD (pH = 7.4): 3.6881962
• Log P: 3.6881983
• Molar Refractivity: 98.6539 cm^3
• Polarizability: 38.85521 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.52
• LOG S: -4.35
• Solubility (Water): 1.54e-02 g/l

PROPERTIES

Physical Property

• Solubility: 22.2mg/L; Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 204-206°C
• Hydrophobicity(logP): 3.5

Safety Information

• Storage Condition: Refrigerator
• RTECS: TU5300000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-48-68
• Safety Statements: 22-24/25
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; 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

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C22H32O3

DETAILS

DrugBank - DB00603

• Drug Groups: approved; investigational
• Description: (6 alpha)-17-Hydroxy-6-methylpregn-4-ene-3,20-dione. A synthetic progestational hormone used in veterinary practice as an estrus regulator. [PubChem]
• Indication: Used as a contraceptive and to treat secondary amenorrhea, abnormal uterine bleeding, pain associated with endometriosis, endometrial and renal cell carcinomas, paraphilia in males, GnRH-dependent forms of precocious puberty, as well as to prevent endometrial changes associated with estrogens.
• Pharmacology: Medroxyprogesterone is a synthetic progestin more potent than progesterone.
• Toxicity: Side effects include loss of bone mineral density, BMD changes in adult women, bleeding irregularities, cancer risks, and thromboembolic disorders.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapidly absorbed from GI tract
• Half Life: 50 days
• Protein Binding: 90%
• Elimination: Following oral dosing, MPA is extensively metabolized in the liver via hydroxylation, with subsequent conjugation and elimination in the urine. Most MPA metabolites are excreted in the urine as glucuronide conjugates with only minor amounts excreted as sulfates.
• Clearance: * 64110 +/- 42662 mL/min [postmenopausal women under fasting conditions with a single Dose of 2 × 10 mg]; * 74123 +/- 35126 mL/min [postmenopausal women under fasting conditions with a single Dose of 8 × 2.5 mg]; * 41963 +/- 38402 mL/min [postmenopausal women following daily administration of one PROVERA 10 mg tablet for 7 days]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M6013

Caution
Much of the pharmacology literature refers to medroxyprogesterone acetate as medroxyprogesterone, but they are of course not the same substance.

Sigma Aldrich - 46411

Caution
Much of the pharmacology literature refers to medroxyprogesterone acetate as medroxyprogesterone, but they are of course not the same substance.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M203550

An orally active progestogen used in hormone replacement therepy (HRT), in the past has been used as a component of oral contraceptives.

REFERENCES

• Pan, Q., et al.: Mol. Hum. Reprod., 13, 797 (2007)
• Matsson, P., et al.: J. Pharmacol. Exp. Ther., 323, 19 (2007)
• Jukosky, J.A., et al.: Bull. Environ. Contam. Toxicol., 81, 230 (2007)
• Cherkasov, A., et al.: J. Med. Chem., 51, 2047 (2007)