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Substance Name: Norethindrone [USP]
RN: 68-22-4
UNII: T18F433X4S
InChIKey: VIKNJXKGJWUCNN-XGXHKTLJSA-N

Note

  • A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception.

Molecular Formula

  • C20-H26-O2

Molecular Weight

  • 298.4234
 

Classification Codes

Classification Codes

  • Contraceptive Agents
  • Contraceptive Agents, Female
  • Contraceptives, Oral
  • Contraceptives, Oral, Synthetic
  • Drug / Therapeutic Agent
  • Hormone
  • Human Data
  • Mutation Data
  • Progestin
  • Reproductive Control Agents
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Norethindrone [USP]
  • Norethisterone [INN]

MeSH Heading

  • Norethindrone

Synonyms

  • (17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one
  • 17-alpha-19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-
  • 17-alpha-Ethinyl-17-beta-hydroxy-delta(sup:4)-estren-3-one
  • 17-alpha-Ethinylestra-4-en-17-beta-ol-3-one
  • 17-alpha-Ethynyl-17-beta-hydroxy-19-norandrost-4-en-3-one
  • 17-alpha-Ethynyl-17-hydroxy-4-estren-3-one
  • 17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one
  • 17-alpha-Ethynyl-19-nortestosterone
  • 17-alpha-Ethynyl-4-estren-17-ol-3-one
  • 17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
  • 17-Ethinyl-19-nortestosterone
  • 17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one
  • 17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one
  • 17alpha-Ethinyl-17beta-hydroxy-delta(sup:4)-estren-3-one
  • 17alpha-Ethinyl-19-nortestosterone
  • 17alpha-Ethinylestra-4-en-17beta-ol-3-one
  • 17alpha-Ethynyl-17-hydroxy-4-estren-3-one
  • 17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one
  • 17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one
  • 17alpha-Ethynyl-19-nortestosterone
  • 17alpha-Ethynyl-4-estren-17-ol-3-one
  • 17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
  • 19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one
  • 19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one
  • 19-Nor-17-alpha-ethynyltestosterone
  • 19-Nor-17-ethinyl testosterone
  • 19-Nor-17-ethinyltestosterone
  • 19-Nor-17alpa-ethynyltestosterone
  • 19-nor-17alpha-Ethynyl-17beta-hydroxy-4-androsten-3-one
  • 19-nor-17alpha-Ethynylandrosten-17beta-ol-3-one
  • 19-nor-17alpha-Ethynyltestosterone
  • 19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-
  • 19-Nor-ethindrone
  • 19-Nor-ethinyl--4,5-testosterone
  • 19-Norethinyltestosterone
  • 19-Norethisterone
  • 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
  • 19-Nortestosterone, 17-ethynyl-
  • 4-08-00-01221 (Beilstein Handbook Reference)
  • AI3-26422
  • Anhydrohydroxynorprogesterone
  • Anovulatorio
  • Anovule
  • Brevinor 21
  • Brevinor 28
  • Brevinor-1 21
  • Brevinor-1 28
  • BRN 1915671
  • Camila
  • CCRIS 484
  • Ciclovulan
  • Conludaf
  • Conludag
  • EC 200-681-6
  • EINECS 200-681-6
  • Errin
  • Estr-4-en-3-one, 17alpha-ethynyl-17-hydroxy-
  • Estrinor
  • Ethinyl-19-nortestosterone
  • Ethinylnortestosterone
  • Ethynylmortestosterone
  • Ethynylnortestosterone
  • Gencept
  • Genora
  • Gestest
  • HSDB 3370
  • Jenest-28
  • Microneth
  • Micronett
  • Micronor
  • Micronovum
  • Milli
  • Mini-pe
  • Mini-pill
  • Minovlar
  • N.E.E.
  • Nelova
  • Nodiol
  • Nor-Q.D.
  • Nor-qd
  • Noraethisteronum
  • Noralutin
  • Norcept-E
  • Norcolut
  • Noresthisterone
  • Norethadrone
  • Norethin
  • Norethindrone
  • Norethisteron
  • Norethisterone
  • Norethisteronum
  • Norethisteronum [INN-Latin]
  • Norethyndron
  • Norethynodron
  • Norethynodrone
  • Noretisterona
  • Noretisterona [INN-Spanish]
  • Noretisterone
  • Noretisterone [DCIT]
  • Norfor
  • Norgestin
  • Noriday
  • Noriday 28
  • Norluten
  • Norlutin
  • Norluton
  • Norpregneninlone
  • Norpregneninotone
  • NSC-9564
  • Orlest
  • Ortho 1 35
  • Ortho 7 7 7
  • Ortho-Novum 1 35
  • Ortho-Novum 1 50
  • Ortho-Novum 7 7 7
  • Ovysmen 0.5 35
  • Ovysmen 1 35
  • Primolut-N
  • Proluteasi
  • SC 4640
  • Synphase
  • Synphasic 28
  • Triella
  • Trinovum 21
  • UNII-T18F433X4S
  • Utovlan
  • Utovlar

Systematic Names

  • 19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-
  • 19-Nor-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy- (8CI)
  • 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
  • Norethisterone

Superlist Names

  • 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17alpha)-
  • Norethindrone
  • Norethisterone
  • Norethisterone [Progestins]

Mixture Names

  • Brevicon
  • Modicon
  • Nora-BE
  • Norethin 1/35 E
  • Norethin 1/50 M
  • Noriday
  • Norinyl
  • Ortho-Novum
  • Ovcon
  • Tri-Norinyl

Registry Numbers

CAS Registry Number

  • 68-22-4

FDA UNII

  • T18F433X4S

System Generated Number

  • 0000068224

Structure Descriptors

InChI

1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

InChIKey

VIKNJXKGJWUCNN-XGXHKTLJSA-N

Smiles

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 809, 1990.
women TDLo oral 42mg/kg (42mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

ENDOCRINE: ANDROGENIC
American Journal of Obstetrics and Gynecology. Vol. 84, Pg. 962, 1962.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 203.5 deg C   EXP
log P (octanol-water) 2.97 (none)   EXP
Water Solubility 7.04 mg/L 25 EXP
Vapor Pressure 7.31E-09 mm Hg 25 EST
Henry's Law Constant 5.80E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.12E-10 cm3/molecule-sec 25 EST

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