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Substance Name: Mestranol [USAN:USP:INN:BAN:JAN]
RN: 72-33-3
UNII: B2V233XGE7
InChIKey: IMSSROKUHAOUJS-MJCUULBUSA-N

Note

  • The 3-methyl ether of ETHINYL ESTRADIOL. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL CONTRACEPTIVES.

Molecular Formula

  • C21-H26-O2

Molecular Weight

  • 310.4344
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Drug / Therapeutic Agent
  • Estrogen
  • Estrogens
  • Hormone
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Out-Dated Pesticide
  • Reproductive Effect
  • Rodenticide
  • Tumor Data

Superlist Classification Code

  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Mestranol
  • Mestranol [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Mestranol

Synonyms

  • (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-estratriene
  • (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene
  • (17-alpha)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol
  • 17-alpha-Ethinyl estradiol 3-methyl ether
  • 17-alpha-Ethinyl oestradiol 3-methyl ether
  • 17-alpha-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17-beta-ol
  • 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-estratriene
  • 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-oestratriene
  • 17-alpha-Ethynyloestradiol methyl ether
  • 17-Ethynyl-3-methoxy-1,3,5(10)-oestratien-17-beta-ol
  • 17-Ethynylestradiol 3-methyl ether
  • 17-Ethynyloestradiol 3-methyl ether
  • 17alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-
  • 17alpha-Ethinyl estradiol 3-methyl ether
  • 17alpha-Ethinyl oestradiol 3-methyl ether
  • 17alpha-Ethinylestradiol 3-methyl ether
  • 17alpha-Ethynylestradiol 3-methyl ether
  • 17alpha-Ethynylestradiol methyl ether
  • 17alpha-Ethynyloestradiol 3-methyl ether
  • 17beta-Estradiol, 17-ethynyl-, 3-(methyl ether)
  • 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene-3-methyl ether
  • 3-Methoxy-17-alpha-19-norpregna-1,3,5(10)-trien-20-yn-17-ol
  • 3-Methoxy-17-alpha-ethinylestradiol
  • 3-Methoxy-17-alpha-ethinyloestradiol
  • 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-estratrien-17-beta-ol
  • 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-oestratrien-17-beta-ol
  • 3-Methoxy-17-alpha-ethynylestradiol
  • 3-Methoxy-17-alpha-ethynyloestradiol
  • 3-Methoxy-17-ethynyloestradiol-17-beta
  • 3-Methoxy-17alpha-ethinylestradiol
  • 3-Methoxy-17alpha-ethinyloestradiol
  • 3-Methoxy-17alpha-ethynyl-1,3,5(10)-estratrien-17beta-ol
  • 3-Methoxy-17alpha-ethynyl-1,3,5(10)-oestratrien-17beta-ol
  • 3-Methoxy-17alpha-ethynylestradiol
  • 3-Methoxy-17alpha-ethynyloestradiol
  • 3-Methoxy-19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol
  • 3-Methoxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol
  • 3-Methoxyethynylestradiol
  • 3-Methoxyethynyloestradiol
  • 3-Methylethynylestradiol
  • 3-Methylethynyloestradiol
  • 3-O-Methylethynylestradiol
  • 33355
  • 4-06-00-06877 (Beilstein Handbook Reference)
  • 8027 C. B.
  • AI3-51798
  • BRN 2625905
  • Caswell No. 547A
  • CCRIS 377
  • Compound 33355
  • delta-MVE
  • Devocin
  • EE(sub3)ME
  • EE3ME
  • EINECS 200-777-8
  • EPA Pesticide Chemical Code 115401
  • Estra-1,3,5(10)-trien-17-beta-ol, 17-alpha-ethynyl-3-methoxy-
  • Estra-1,3,5(10)-trien-17beta-ol, 17-ethynyl-3-methoxy-
  • Ethinylestradiol 3-methyl ether
  • Ethinyloestradiol 3-methyl ether
  • Ethynylestradiol 3-methyl ether
  • Ethynylestradiol methyl ether
  • Ethynyloestradiol 3-methyl ether
  • HSDB 3588
  • Inostral
  • Inostral (steroid)
  • Menophase
  • Mestranol
  • Mestranolo
  • Mestranolo [DCIT]
  • Mestranolum
  • Mestranolum [INN-Latin]
  • Norquen
  • NSC 84032
  • Ovastol
  • SC 4725
  • UNII-B2V233XGE7

Systematic Names

  • 17-alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-
  • 19-Nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-
  • 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17alpha)-
  • Mestranol

Superlist Names

  • 19-Nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-
  • Mestranol
  • Mestranol [Steroidal oestrogens]

Mixture Names

  • Enovid
  • Norethin 1/50 M
  • Norinyl
  • Norquen
  • Ortho-Novum
  • Ovulen

Registry Numbers

CAS Registry Number

  • 72-33-3

FDA UNII

  • B2V233XGE7

Other Registry Numbers

  • 43085-54-7
  • 53445-46-8

System Generated Number

  • 0000072333

Structure Descriptors

InChI

1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

InChIKey

IMSSROKUHAOUJS-MJCUULBUSA-N

Smiles

C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@]2(C#C)O)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 3200mg/kg (3200mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
mouse LD50 oral > 10gm/kg (10000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
mouse LD50 subcutaneous 2500mg/kg (2500mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
rat LD50 intraperitoneal > 3gm/kg (3000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
rat LD50 oral > 10gm/kg (10000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 150.5 deg C   EXP
log P (octanol-water) 4.680 (none)   EST
Atmospheric OH Rate Constant 9.04E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.