norethisterone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
steroids, progestogens 1962 68-22-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • norethindrone
  • norethisteron
  • norethisterone
  • norethynodrone
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 weight: 298.43
  • Formula: C20H26O2
  • CLOGP: 2.79
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 37.30
  • ALOGS: -4.65
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2.50 mg P
5 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.02 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 64 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 21, 1962 FDA ORTHO MCNEIL PHARM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dilatation intrahepatic duct acquired 230.26 47.86 26 252 62 2357745
Vaginal haemorrhage 155.25 47.86 31 247 4949 2352858
Purpura 131.22 47.86 23 255 1787 2356020
Hepatotoxicity 128.48 47.86 25 253 3456 2354351
Venoocclusive liver disease 125.34 47.86 19 259 589 2357218
Rash maculo-papular 117.53 47.86 24 254 4228 2353579
Rectal haemorrhage 104.28 47.86 23 255 5833 2351974
Rash erythematous 103.81 47.86 23 255 5953 2351854
Melaena 100.66 47.86 21 257 4085 2353722
Haemorrhage 94.73 47.86 24 254 11015 2346792
Hepatic adenoma 88.56 47.86 11 267 70 2357737
Cholestasis of pregnancy 83.79 47.86 11 267 114 2357693
Liver function test abnormal 82.88 47.86 20 258 7470 2350337
Alanine aminotransferase increased 79.62 47.86 22 256 14010 2343797
Haemoglobin decreased 74.02 47.86 22 256 18129 2339678
Platelet count increased 57.89 47.86 12 266 2225 2355582
Cerebral venous thrombosis 48.32 47.86 8 270 430 2357377
Ovarian atrophy 48.01 47.86 6 272 40 2357767

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC G03AC01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens
ATC G03DC02 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS
Estren derivatives
ATC G03AA05 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, fixed combinations
ATC G03AB04 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, sequential preparations
ATC G03FA01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, fixed combinations
ATC G03FB05 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, sequential preparations
FDA Chemical/Ingredient N0000011301 Progesterone Congeners
FDA EPC N0000175602 Progestin
CHEBI has role CHEBI:49326 synthetic oral contraceptive
MeSH PA D003270 Contraceptive Agents
MeSH PA D003271 Contraceptive Agents, Female
MeSH PA D000080066 Contraceptive Agents, Hormonal
MeSH PA D003278 Contraceptives, Oral, Hormonal
MeSH PA D003280 Contraceptives, Oral, Synthetic
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Contraception indication 13197004
Female hypogonadism syndrome indication 16041008
Dysfunctional uterine bleeding indication 19155002
Atrophic vaginitis indication 52441000
Primary ovarian failure indication 65846009
Secondary physiologic amenorrhea indication 86030004
Acne vulgaris indication 88616000
Postmenopausal osteoporosis indication 102447009
Endometriosis indication 129103003
Menopausal flushing indication 198436008
Atrophic vulva indication 248861000 DOID:14275
Menorrhagia indication 386692008
Amenorrhea off-label use 14302001 DOID:13938
Polycystic ovaries off-label use 69878008
Dysmenorrhea off-label use 266599000
Abnormal uterine bleeding unrelated to menstrual cycle off-label use 312984006
Heart valve disorder contraindication 368009 DOID:4079
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Depressive disorder contraindication 35489007
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Chronic heart failure contraindication 48447003
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Hyperlipidemia contraindication 55822004 DOID:1168
Benign mammary dysplasia contraindication 57993004
Obstructive hyperbilirubinemia contraindication 59848001
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Kidney disease contraindication 90708001 DOID:557
Malignant neoplasm of liver contraindication 93870000 DOID:3571
Uterine leiomyoma contraindication 95315005 DOID:13223
Deep venous thrombosis contraindication 128053003
Liver function tests abnormal contraindication 166603001
Mammography abnormal contraindication 168750009
Angina pectoris contraindication 194828000
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Cholestasis of pregnancy contraindication 235888006
Endometrial carcinoma contraindication 254878006 DOID:2871
Chorea contraindication 271700006
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Malignant tumor of cervix contraindication 363354003 DOID:4362
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Cardiovascular event risk contraindication 395112001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Porphyria contraindication 418470004
Optic disc edema contraindication 423341008 DOID:146
Family history of malignant neoplasm of breast contraindication 429740004
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002
Nonspecific Abnormal Papanicolaou Smear of Cervix contraindication
Major Surgery with Prolonged Post-Operative Immobilization contraindication

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Progesterone receptor Nuclear hormone receptor AGONIST ED50 11.26 WOMBAT-PK CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 5.62 DRUG MATRIX
Glucocorticoid receptor Nuclear hormone receptor Ki 6.71 DRUG MATRIX
Estrogen receptor Nuclear hormone receptor Ki 6.64 DRUG MATRIX
Sex hormone-binding globulin Secreted Kd 7.97 CHEMBL
Androgen receptor Nuclear hormone receptor IC50 7.12 WOMBAT-PK
Progesterone receptor Transcription factor Ki 8.91 DRUG MATRIX
Estrogen receptor Transcription factor Kd 9.20 CHEMBL
Androgen receptor Transcription factor IC50 6.92 CHEMBL

External reference:

IDSource
4018496 VUID
N0000146818 NUI
C0028356 UMLSCUI
D00182 KEGG_DRUG
63758001 SNOMEDCT_US
4018496 VANDF
7514 RXNORM
126102009 SNOMEDCT_US
5187 MMSL
d00555 MMSL
182290 MMSL
001298 NDDF
001326 NDDF
CHEBI:7627 CHEBI
CHEMBL1162 ChEMBL_ID
DB00717 DRUGBANK_ID
T18F433X4S UNII
687 INN_ID
6230 PUBCHEM_CID
D009640 MESH_DESCRIPTOR_UI
2880 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
GENERESS Fe HUMAN PRESCRIPTION DRUG LABEL 3 0023-6030 KIT 0.80 mg ORAL NDA 19 sections
Norethindrone HUMAN PRESCRIPTION DRUG LABEL 1 0378-7272 TABLET 0.35 mg ORAL ANDA 13 sections
NORETHINDRONE HUMAN PRESCRIPTION DRUG LABEL 1 0378-7292 TABLET 0.35 mg ORAL ANDA 13 sections
NORETHINDRONE AND ETHINYL ESTRADIOL AND FERROUS FUMARATE HUMAN PRESCRIPTION DRUG LABEL 2 0378-7297 KIT 0.40 mg None ANDA 19 sections
NORETHINDRONE AND ETHINYL ESTRADIOL AND FERROUS FUMARATE HUMAN PRESCRIPTION DRUG LABEL 2 0378-7308 KIT 0.80 mg None ANDA 19 sections
Nortrel HUMAN PRESCRIPTION DRUG LABEL 2 0555-9008 KIT 0.50 mg None ANDA 14 sections
Nortrel HUMAN PRESCRIPTION DRUG LABEL 2 0555-9009 TABLET 1 mg ORAL ANDA 14 sections
Nortrel HUMAN PRESCRIPTION DRUG LABEL 2 0555-9010 KIT 1 mg None ANDA 14 sections
Nortrel 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 0555-9012 KIT 0.75 mg None ANDA 15 sections
Nortrel 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 0555-9012 KIT 1 mg None ANDA 15 sections
Nortrel 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 0555-9012 KIT 0.50 mg None ANDA 15 sections
Balziva HUMAN PRESCRIPTION DRUG LABEL 2 0555-9034 KIT 0.40 mg None ANDA 14 sections
Aranelle HUMAN PRESCRIPTION DRUG LABEL 4 0555-9066 KIT 1 mg None ANDA 14 sections
Aranelle HUMAN PRESCRIPTION DRUG LABEL 4 0555-9066 KIT 0.50 mg None ANDA 14 sections
Cyclafem 1/35 HUMAN PRESCRIPTION DRUG LABEL 2 0603-7521 KIT 1 mg None ANDA 16 sections
Cyclafem 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 0603-7525 KIT 1 mg None ANDA 16 sections
Cyclafem 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 0603-7525 KIT 0.75 mg None ANDA 16 sections
Cyclafem 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 0603-7525 KIT 0.50 mg None ANDA 16 sections
Dasetta 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 16714-346 KIT 1 mg ORAL ANDA 15 sections
Dasetta 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 16714-346 KIT 0.50 mg ORAL ANDA 15 sections
Dasetta 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 6 16714-346 KIT 0.75 mg ORAL ANDA 15 sections
Philith HUMAN PRESCRIPTION DRUG LABEL 2 16714-347 KIT 0.40 mg ORAL ANDA 13 sections
Dasetta 1/35 HUMAN PRESCRIPTION DRUG LABEL 2 16714-348 KIT 1 mg ORAL ANDA 14 sections
Wera HUMAN PRESCRIPTION DRUG LABEL 2 16714-370 KIT 0.50 mg ORAL ANDA 15 sections
DEBLITANE HUMAN PRESCRIPTION DRUG LABEL 1 16714-440 KIT 0.35 mg None ANDA 14 sections
SHAROBEL HUMAN PRESCRIPTION DRUG LABEL 1 16714-441 KIT 0.35 mg None ANDA 14 sections
Necon HUMAN PRESCRIPTION DRUG LABEL 2 21695-857 KIT 1 mg None ANDA 13 sections
Necon 0.5/35 HUMAN PRESCRIPTION DRUG LABEL 2 42254-287 KIT 0.50 mg None ANDA 14 sections
ALYACEN 1/35 HUMAN PRESCRIPTION DRUG LABEL 2 50090-1477 KIT 1 mg None ANDA 12 sections
ALYACEN 7/7/7 HUMAN PRESCRIPTION DRUG LABEL 2 50090-1478 KIT 0.50 mg None ANDA 12 sections