norethisterone ๐Ÿถ Veterinary Use | 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 ยตM/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
Vaginal haemorrhage 118.83 19.22 56 5298 24495 50575275
Hepatic adenoma 103.60 19.22 19 5335 265 50599505
Endometriosis 53.39 19.22 19 5335 4056 50595714
Pelvic pain 49.41 19.22 24 5330 11189 50588581
Purpura 49.12 19.22 23 5331 9888 50589882
Heavy menstrual bleeding 42.04 19.22 24 5330 15513 50584257
Pregnancy on oral contraceptive 40.67 19.22 11 5343 947 50598823
Intermenstrual bleeding 40.67 19.22 18 5336 6796 50592974
Exposure to allergen 39.75 19.22 8 5346 186 50599584
Rash erythematous 32.51 19.22 28 5326 34824 50564946
Rash maculo-papular 32.43 19.22 25 5329 26616 50573154
Ovarian atrophy 32.36 19.22 6 5348 89 50599681
Uterine perforation 32.13 19.22 15 5339 6400 50593370
Drug-induced liver injury 29.14 19.22 24 5330 28071 50571699
Aplastic anaemia 26.64 19.22 14 5340 7689 50592081
Cerebral venous sinus thrombosis 26.57 19.22 9 5345 1659 50598111
Genital burning sensation 26.55 19.22 6 5348 245 50599525
Hereditary angioedema 25.03 19.22 12 5342 5430 50594340
Superior sagittal sinus thrombosis 24.85 19.22 7 5347 700 50599070
Rectal haemorrhage 24.44 19.22 25 5329 38533 50561237
Vaginal ulceration 24.24 19.22 6 5348 364 50599406
Haemorrhage 24.12 19.22 29 5325 53412 50546358
Hot flush 23.34 19.22 26 5328 44143 50555627
Injury 22.82 19.22 27 5327 48898 50550872
Lip exfoliation 22.29 19.22 6 5348 507 50599263
Migraine 21.93 19.22 33 5321 75247 50524523
Melaena 21.89 19.22 20 5334 26844 50572926
Pruritus genital 21.11 19.22 6 5348 620 50599150
Dilatation intrahepatic duct acquired 20.93 19.22 6 5348 639 50599131
Transfusion 19.97 19.22 14 5340 12891 50586879

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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
Vaginal haemorrhage 132.44 20.58 49 4106 19295 64475282
Hepatic adenoma 92.26 20.58 16 4139 271 64494306
Heavy menstrual bleeding 45.76 20.58 20 4135 12057 64482520
Purpura 44.85 20.58 22 4133 17224 64477353
Pelvic pain 44.39 20.58 19 4136 10891 64483686
Exposure to allergen 43.59 20.58 8 4147 189 64494388
Pregnancy on oral contraceptive 43.11 20.58 10 4145 761 64493816
Uterine perforation 37.08 20.58 14 4141 5806 64488771
Ovarian atrophy 35.53 20.58 6 4149 86 64494491
Intermenstrual bleeding 35.10 20.58 13 4142 5112 64489465
Endometriosis 34.44 20.58 11 4144 2781 64491796
Rash erythematous 30.11 20.58 25 4130 48608 64445969
Vaginal ulceration 29.79 20.58 6 4149 234 64494343
Genital burning sensation 28.82 20.58 6 4149 276 64494301
Drug-induced liver injury 28.48 20.58 24 4131 47619 64446958
Rash maculo-papular 26.70 20.58 23 4132 47003 64447574
Superior sagittal sinus thrombosis 26.06 20.58 7 4148 969 64493608
Cerebral venous sinus thrombosis 25.76 20.58 8 4147 1847 64492730
Injury 25.14 20.58 24 4131 55968 64438609
Ovarian failure 24.89 20.58 6 4149 539 64494038
Lip exfoliation 24.71 20.58 6 4149 555 64494022
Migraine 24.67 20.58 25 4130 62652 64431925
Maternal exposure during pregnancy 23.66 20.58 30 4125 95854 64398723
Dilatation intrahepatic duct acquired 23.45 20.58 6 4149 688 64493889
Rectal haemorrhage 23.14 20.58 24 4131 61793 64432784
Aplastic anaemia 22.68 20.58 13 4142 13907 64480670
Transfusion 22.06 20.58 14 4141 17980 64476597
Pruritus genital 21.09 20.58 6 4149 1026 64493551

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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 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 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
ATC H01CC54 SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES
HYPOTHALAMIC HORMONES
Anti-gonadotropin-releasing hormones
FDA CS M0447349 Progesterone Congeners
FDA EPC N0000175602 Progestin
FDA Chemical/Ingredient N0000011301 Progesterone Congeners
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
CHEBI has role CHEBI:49326 synthetic oral contraceptives
CHEBI has role CHEBI:59826 progestins

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Glucocorticoid receptor Nuclear hormone receptor Ki 6.71 DRUG MATRIX
Estrogen receptor Nuclear hormone receptor Ki 6.64 DRUG MATRIX
Androgen receptor Nuclear hormone receptor IC50 7.12 WOMBAT-PK
Sex hormone-binding globulin Secreted Kd 7.97 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 5.62 DRUG MATRIX
Androgen receptor Transcription factor IC50 6.92 CHEMBL
Progesterone receptor Transcription factor Ki 8.91 DRUG MATRIX
Estrogen receptor Transcription factor Kd 9.20 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Norethindrone HUMAN PRESCRIPTION DRUG LABEL 1 0378-7272 TABLET 0.35 mg ORAL ANDA 14 sections
Norethindrone HUMAN PRESCRIPTION DRUG LABEL 1 0378-7272 TABLET 0.35 mg ORAL ANDA 14 sections
NORETHINDRONE HUMAN PRESCRIPTION DRUG LABEL 1 0378-7292 TABLET 0.35 mg ORAL ANDA 14 sections
Nortrel21 Day HUMAN PRESCRIPTION DRUG LABEL 2 0555-9009 TABLET 1 mg ORAL ANDA 21 sections
LYZA HUMAN PRESCRIPTION DRUG LABEL 1 50102-100 TABLET 0.35 mg ORAL ANDA 13 sections
Tulana Human Prescription Drug Label 1 50102-200 TABLET 0.35 mg ORAL ANDA 14 sections
Lyleq Human Prescription Drug Label 1 50102-300 TABLET 0.35 mg ORAL ANDA 14 sections
Ortho Micronor HUMAN PRESCRIPTION DRUG LABEL 1 50458-194 TABLET 0.35 mg ORAL NDA 24 sections
NORLYROC HUMAN PRESCRIPTION DRUG LABEL 1 51660-127 TABLET, FILM COATED 0.35 mg ORAL ANDA 12 sections
CAMILA HUMAN PRESCRIPTION DRUG LABEL 1 51862-884 TABLET 0.35 mg ORAL ANDA 25 sections
ERRIN HUMAN PRESCRIPTION DRUG LABEL 1 51862-886 TABLET 0.35 mg ORAL ANDA 26 sections
ERRIN HUMAN PRESCRIPTION DRUG LABEL 1 51862-886 TABLET 0.35 mg ORAL ANDA 26 sections
Nora BE HUMAN PRESCRIPTION DRUG LABEL 1 52544-629 TABLET 0.35 mg ORAL NDA authorized generic 19 sections
Jolivette HUMAN PRESCRIPTION DRUG LABEL 1 52544-892 TABLET 0.35 mg ORAL NDA 27 sections
Lyleq Human Prescription Drug Label 1 53002-1793 TABLET 0.35 mg ORAL ANDA 14 sections
Tulana Human Prescription Drug Label 1 53002-2687 TABLET 0.35 mg ORAL ANDA 14 sections
MICRONOR HUMAN PRESCRIPTION DRUG LABEL 1 54868-4369 TABLET 0.35 mg ORAL NDA 14 sections
Camila HUMAN PRESCRIPTION DRUG LABEL 1 54868-4814 TABLET 0.35 mg ORAL ANDA 15 sections
NORETHINDRONE HUMAN PRESCRIPTION DRUG LABEL 1 57297-876 TABLET 0.35 mg ORAL ANDA 13 sections
Jencycla HUMAN PRESCRIPTION DRUG LABEL 1 57297-877 TABLET 0.35 mg ORAL ANDA 14 sections
Norethindrone HUMAN PRESCRIPTION DRUG LABEL 1 63187-748 TABLET 0.35 mg ORAL ANDA 24 sections
Incassia Human Prescription Drug Label 1 65862-925 TABLET 0.35 mg ORAL ANDA 14 sections
AMABELZ HUMAN PRESCRIPTION DRUG LABEL 2 68180-829 TABLET 0.10 mg ORAL ANDA 30 sections
AMABELZ HUMAN PRESCRIPTION DRUG LABEL 2 68180-829 TABLET 0.10 mg ORAL ANDA 30 sections
AMABELZ HUMAN PRESCRIPTION DRUG LABEL 2 68180-830 TABLET 0.50 mg ORAL ANDA 30 sections
AMABELZ HUMAN PRESCRIPTION DRUG LABEL 2 68180-830 TABLET 0.50 mg ORAL ANDA 30 sections
NORETHINDRONE HUMAN PRESCRIPTION DRUG LABEL 1 68180-876 TABLET 0.35 mg ORAL ANDA 13 sections
NORETHINDRONE HUMAN PRESCRIPTION DRUG LABEL 1 68180-876 TABLET 0.35 mg ORAL ANDA 13 sections
Jencycla HUMAN PRESCRIPTION DRUG LABEL 1 68180-877 TABLET 0.35 mg ORAL ANDA 14 sections
Jencycla HUMAN PRESCRIPTION DRUG LABEL 1 68180-877 TABLET 0.35 mg ORAL ANDA 14 sections