Identification

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Name
Norethisterone
Accession Number
DB00717  (APRD00679)
Type
Small Molecule
Groups
Approved
Description

Norethisterone (INN, BAN), also known as Norethindrone (USAN), is 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.

Structure
Thumb
Synonyms
  • (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one
  • 17-hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one
  • 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one
  • 17-α-ethynyl-17-hydroxy-4-estren-3-one
  • 17-α-ethynyl-19-norandrost-4-en-17-β-ol-3-one
  • 17-α-ethynyl-19-nortestosterone
  • 17-α-ethynyl-4-estren-17-ol-3-one
  • 17-β-hydroxy-19-norpregn-4-en-20-yn-3-one
  • 17α-ethinyl-19-nortestosterone
  • 17α-ethinylestra-4-en-17β-ol-3-one
  • 17α-ethynyl-17-hydroxy-4-estren-3-one
  • 17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one
  • 17α-ethynyl-19-nor-4-androsten-17β-ol-3-one
  • 17α-ethynyl-19-norandrost-4-en-17β-ol-3-one
  • 17α-ethynyl-19-nortestosterone
  • 17α-ethynyl-4-estren-17-ol-3-one
  • 17β-hydroxy-19-norpregn-4-en-20-yn-3-one
  • 19-nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-one
  • 19-nor-17-α-ethynylandrosten-17-β-ol-3-one
  • 19-nor-17-α-ethynyltestosterone
  • 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one
  • 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one
  • 19-nor-17α-ethynylandrosten-17β-ol-3-one
  • 19-nor-17α-ethynyltestosterone
  • 19-nor-ethindrone
  • 19-norethisterone
  • 4-estren-17α-ethynyl-17β-ol-3-one
  • Norethindrone
  • Norethisteron
  • Noréthistérone
  • Norethisterone
  • Norethisteronum
  • Noretisterona
External IDs
NSC-9564 / SC-4640
Product Ingredients
IngredientUNIICASInChI Key
Norethisterone acetate9S44LIC7OJ51-98-9IMONTRJLAWHYGT-ZCPXKWAGSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
JencyclaTablet0.35 mgOralLupin Pharma2015-09-14Not applicableCanada
JolivetteTablet0.35 mg/1OralActavis Pharma, Inc.2003-03-012020-12-31Us52544 0892 28 nlmimage10 5f45afed
MicronorTablet0.35 mg/1OralPhysicians Total Care, Inc.2003-09-17Not applicableUs
Micronor Tablets 28-dayTabletOralJanssen Pharmaceuticals1972-12-31Not applicableCanada
MovisseTabletOralMylan Pharmaceuticals2015-06-30Not applicableCanada
Nor QDTablet0.35 mg/1OralPhysicians Total Care, Inc.1973-01-022010-06-30Us
Nor QDTablet0.35 mg/1OralWatson Pharma, Inc.1973-01-022018-06-13Us
Nora-BETablet0.35 mg/1OralWatson Pharmaceuticals, Inc.2006-04-122006-04-12Us
Norethindrone Tablets, USPTabletOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada
NorlutateTabletOralErfa Canada 2012 Inc1961-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AygestinTablet5 mg/1OralTeva Women's Health, Inc.2003-06-12Not applicableUs51285 0424 10 nlmimage10 562f2b09
CamilaTablet0.35 mg/1OralMayne Pharma Inc.2016-08-032020-04-30Us
CamilaTablet0.35 mg/1OralMayne Pharma2018-06-15Not applicableUs
CamilaTablet0.35 mg/1OralTeva2002-10-302018-02-28Us00555 0715 58 nlmimage10 fb2f7deb
CamilaTablet0.35 mg/1OralPhysicians Total Care, Inc.2003-06-19Not applicableUs54868 481420180906 25352 1kr5t05
DeblitaneKit0.35 mg/1OralNorthStar Rx LLC2013-09-13Not applicableUs
ErrinTablet0.35 mg/1OralMayne Pharma Inc.2016-08-032020-04-30Us
ErrinTablet0.35 mg/1OralMayne Pharma2018-04-18Not applicableUs
ErrinTablet0.35 mg/1OralTeva Pharmaceuticals USA, Inc.2003-01-082019-03-31Us00555 0344 58 nlmimage10 20369034
HeatherTablet0.35 mg/1OralGlenmark Pharmaceuticals Inc., USA2010-04-23Not applicableUs68462 0303 29 nlmimage10 5745ab9d
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ActivellaNorethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralGemini Laboratories, LLC2016-05-122020-07-31Us
ActivellaNorethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralAmneal Pharmaceuticals LLC2019-05-01Not applicableUs
ActivellaNorethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralNovo Nordisk2003-07-222018-10-31Us
ActivellaNorethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1)Tablet, film coatedOralGemini Laboratories, LLC2016-05-122019-08-31Us
ActivellaNorethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1)Tablet, film coatedOralGemini Laboratories, LLC2019-03-04Not applicableUs
ActivellaNorethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1)Tablet, film coatedOralNovo Nordisk2007-04-092017-04-30Us
ActivelleNorethisterone acetate (0.5 mg) + Estradiol (1.0 mg)TabletOralNovo Nordisk2008-05-16Not applicableCanada
Activelle LdNorethisterone acetate (0.1 mg) + Estradiol (0.5 mg)TabletOralNovo Nordisk2008-05-16Not applicableCanada
Alyacen 1/35Norethisterone (1 mg/1) + Ethinylestradiol (0.035 mg/1)KitOralGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUs
Alyacen 1/35Norethisterone (1 mg/1) + Ethinylestradiol (0.035 mg/1)KitOralRemedy Repack2018-05-16Not applicableUs
International/Other Brands
Conludag / Micronovum / Mini-PE / Mini-pill / Norcolut / Noriday / Norluten / Norlutin / Primolut-N / Utovlan
Categories
UNII
T18F433X4S
CAS number
68-22-4
Weight
Average: 298.4192
Monoisotopic: 298.193280076
Chemical Formula
C20H26O2
InChI Key
VIKNJXKGJWUCNN-XGXHKTLJSA-N
InChI
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
IUPAC Name
(1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

Pharmacology

Indication

For the treatment of secondary amenorrhea, endometriosis, and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer.

Associated Conditions
Associated Therapies
Pharmacodynamics

Norethindrone is a synthetic oral progestin. It is used for contraception or to treat such conditions as secondary amenorrhea, abnormal uterine bleeding, and endometriosis. As an oral contraceptive, norethindrone is available as either a single agent or in combination with an estrogen. Norethindrone acetate induces secretory changes in an estrogen-primed endometrium. On a weight basis, it is twice as potent as norethindrone.

Mechanism of action

Progestins diffuse freely into target cells and bind to the progesterone receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge.

TargetActionsOrganism
UProgesterone receptor
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Norethindrone acetate is completely and rapidly deacetylated to norethindrone (NET) after oral administration, and the disposition of norethindrone acetate is indistinguishable from that of orally administered norethindrone. Norethindrone is rapidly absorbed from norethindrone acetate, in which maximum plasma concentration occur 2 hours post-dose (Tmax). When a single dose is given to healthy women, the Cmax is 26.19 ± 6.19 hours. The AUC (0-inf) is 166.90 ± 56.28 ng/mL*h. Absolute oral bioavailability is approximately 64%. The effect of food on the pharmacokinetics of norethindrone acetate is unknown.

Volume of distribution
  • 4 L/kg
Protein binding

Norethindrone is 36% bound to sex hormone-binding globulin and 61% bound to albumin.

Metabolism

Hepatic. Norethindrone is extensively metabolized, primarily via reduction. It also undergoes sulfate and glucuronide conjugation. The majority of metabolites in the circulation are sulfates, with glucuronides accounting for most of the urinary metabolites.

Route of elimination

Norethindrone is excreted in both urine and feces, primarily as metabolites.

Half life

8.51 ± 2.19 (when a single dose is given to healthy women)

Clearance
  • 0.4 L/hr/kg [plasma clearance]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinNorethisterone may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinNorethisterone may decrease the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Norethisterone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Norethisterone.
4-OxoretinolThe therapeutic efficacy of Norethisterone can be decreased when used in combination with 4-Oxoretinol.
6-Deoxyerythronolide BThe metabolism of Norethisterone can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecinThe metabolism of Norethisterone can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
7-NitroindazoleThe metabolism of Norethisterone can be increased when combined with 7-Nitroindazole.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Norethisterone.
AbataceptThe metabolism of Norethisterone can be increased when combined with Abatacept.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
  • Take without regard to meals.

References

General References
  1. Stanczyk FZ, Roy S: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. [PubMed:2143719]
  2. DPD Approved Drugs: Jencycla oral tablets [Link]
External Links
Human Metabolome Database
HMDB0014855
KEGG Drug
D00182
KEGG Compound
C05028
PubChem Compound
6230
PubChem Substance
46504816
ChemSpider
5994
BindingDB
50148732
ChEBI
7627
ChEMBL
CHEMBL1162
Therapeutic Targets Database
DAP001212
PharmGKB
PA450651
HET
NDR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Norethisterone
ATC Codes
G03DC02 — NorethisteroneG03AA05 — Norethisterone and ethinylestradiolG03AB04 — Norethisterone and ethinylestradiolG03AC01 — NorethisteroneG03FA01 — Norethisterone and estrogenG03FB05 — Norethisterone and estrogen
AHFS Codes
  • 68:12.00 — Contraceptives
  • 68:32.00 — Progestins
PDB Entries
1sqn / 2w8y

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableBioequivalence1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Ethinyl Estradiol and Norethindrone / Pharmacokinetics of Isavuconazole1
1CompletedNot AvailableHepatitis C Viral Infection1
1CompletedBasic SciencePharmacokinetics1
1CompletedOtherBiological Availability1
1CompletedOtherHealthy Female Volunteers / Type 2 Diabetes Mellitus1
1CompletedTreatmentArthritic Psoriasis / Inflammatory Bowel Diseases (IBD) / Psoriasis / Systemic Lupus Erythematosus (SLE)1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers / Menopause2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedTreatmentRheumatoid Arthritis1
1CompletedTreatmentSolid Cancers1
1CompletedTreatmentTumors, Solid1
1CompletedTreatmentType 2 Diabetes Mellitus1
1WithdrawnTreatmentMalignancies1
2CompletedTreatmentContraception1
2CompletedTreatmentEndometrial Hyperplasia1
2CompletedTreatmentEndometriosis2
2CompletedTreatmentHeavy Uterine Bleeding / Uterine Leiomyomas2
2CompletedTreatmentHyperandrogenism1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive / Relapsing Remitting Multiple Sclerosis (RRMS) / Secondary Progressive Multiple Sclerosis (SPMS)1
2Unknown StatusTreatmentEndometrial Cancers / Endometrial Hyperplasia1
2, 3CompletedPreventionAlkylating Agents / Fertility Preservation / Malignant Lymphomas1
3Active Not RecruitingTreatmentEndometriosis1
3Active Not RecruitingTreatmentEndometriosis related pain1
3Active Not RecruitingTreatmentHeavy Menstrual Bleeding / Uterine Leiomyomas6
3CompletedPreventionContraception2
3CompletedPreventionContraceptive Usage1
3CompletedPreventionPrevention of Pregnancy1
3CompletedSupportive CareBreast Cancer / Menopausal Symptoms1
3CompletedTreatmentEndometriosis / Pelvic Pain1
3CompletedTreatmentHealthy Volunteers2
3CompletedTreatmentHeavy Menstrual Bleeding / Uterine Leiomyomas1
3CompletedTreatmentMenopausal Vasomotor Symptoms / Menopause1
3CompletedTreatmentMenstrual Cramps2
3CompletedTreatmentRheumatoid Arthritis1
3CompletedTreatmentSexual Dysfunctions1
3CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
3CompletedTreatmentOne to five years postmenopausal1
3Enrolling by InvitationTreatmentEndometriosis / Endometriosis related pain1
3Enrolling by InvitationTreatmentUterine Leiomyomas1
3Not Yet RecruitingTreatmentEndometriosis1
3RecruitingBasic ScienceContraception / Ovulation1
3RecruitingTreatmentEndometriosis related pain1
3TerminatedTreatmentEndometriosis1
3Unknown StatusTreatmentEndometriosis / Menstrual Cramps / Painful Intercourse1
4CompletedBasic ScienceContraception / Fertility1
4CompletedPreventionMenstrual Flow Altered1
4CompletedTreatmentHealthy Volunteers / Menopause1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Hyperuricemia / Menopause1
4CompletedTreatmentMenopause1
4CompletedTreatmentPremature Ovarian Failure (POF)1
4RecruitingPreventionBacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV)1
4RecruitingTreatmentEndometriosis / Interstitial Cystitis / Menstrual Cramps / Migraine Disorders / Pain, Chronic / Pelvic Pain / Visceral Pain1
4TerminatedPreventionMenopause1
4Unknown StatusPreventionPostpartum Depressive Mood / Postpartum Sexual Function1
4Unknown StatusTreatmentHeavy Menstrual Bleeding / Hypermenorrhea1
4Unknown StatusTreatmentHormone Replacement Therapy1
Not AvailableActive Not RecruitingNot AvailableContraception / Human Immunodeficiency Virus (HIV) / Immune Cells (Mucosal and Systemic) / Microbiota1
Not AvailableActive Not RecruitingTreatmentEtonogestrel Contraceptive Implant, Bothersome Bleeding1
Not AvailableCompletedNot AvailableMenopause / Postmenopausal haemorrhage1
Not AvailableCompletedNot AvailablePulmonary Embolism / Sinus Thrombosis, Intracranial / Thrombosis, Venous1
Not AvailableCompletedBasic ScienceCystic Fibrosis (CF)1
Not AvailableCompletedBasic ScienceOral Contraceptives (OC)1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Pregnancy1
Not AvailableCompletedTreatmentEmotional / Headache / Pelvic Pain1
Not AvailableCompletedTreatmentEndometrial Hyperplasia1
Not AvailableCompletedTreatmentHypermenorrhea1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableRecruitingNot AvailableContraceptive / Contraceptive Effectiveness1
Not AvailableTerminatedPreventionDisorders, Blood Coagulation / Women's Health1
Not AvailableUnknown StatusBasic ScienceOral Contraceptives (OC)1
Not AvailableWithdrawnPreventionEndometriotic Cysts1
Not AvailableWithdrawnTreatmentIVF Poor Responders1

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
  • Barr laboratories inc
  • Glenmark generics ltd
  • Ortho mcneil janssen pharmaceuticals inc
  • Watson laboratories inc
  • Duramed research inc
  • Glenmark generics ltd india
  • Warner Chilcott
Packagers
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Breckenridge Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Glenmark Generics Ltd.
  • Innovative Manufacturing and Distribution Services Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Novartis AG
  • Noven Pharmaceuticals Inc.
  • Novo Nordisk Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Patheon Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmaceutics International Inc.
  • Pharmacia Inc.
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Qualitest
  • Quality Care
  • Redpharm Drug
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Warner Chilcott Co. Inc.
  • Watson Pharmaceuticals
  • WC Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral0.35 mg/1
Patch, extended releaseTransdermal
PatchTransdermal
Tablet, film coatedOral
TabletOral
Tablet, chewableOral
TabletOral0.35 mg
KitOral
KitTopical
TabletOral
KitOral0.35 mg/1
TabletOral5 mg/1
Tablet, film coatedOral0.35 mg/1
Prices
Unit descriptionCostUnit
Ovcon-35 (28) 28 0.4-35 mg-mcg tablet Disp Pack89.09USD disp
Ovcon-50 28 50-1 mcg-mg tablet Disp Pack89.09USD disp
Loestrin 1.5/30 (21) 21 1.5-30 mg-mcg tablet Disp Pack79.32USD disp
Loestrin 1/20 (21) 21 1-20 mg-mcg tablet Disp Pack79.32USD disp
Loestrin Fe 1/20 28 1-20 mg-mcg tablet Disp Pack79.32USD disp
Loestrin Fe 1.5/30 28 1.5-30 mg-mcg tablet Disp Pack77.1USD disp
Loestrin 24 Fe 28 1-20 mg-mcg tablet Disp Pack75.15USD disp
Nor-QD 28 0.35 mg tablet Disp Pack65.87USD disp
Tri-Norinyl (28) 28 0.5/1/0.5-35 mg-mcg tablet Disp Pack62.63USD disp
Ortho-Novum 10/11 (28) 28 35 mcg tablet Disp Pack60.25USD disp
Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack59.99USD disp
Norinyl 1+35 (28) 28 1-35 mg-mcg tablet Disp Pack55.99USD disp
Ortho-Novum 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack55.99USD disp
Brevicon (28) 28 0.5-35 mg-mcg tablet Disp Pack53.0USD disp
Norinyl 1+50 (28) 28 1-50 mg-mcg tablet 1 Disp Pack = 28 Pills52.99USD disp
Necon 10/11 (28) 28 35 mcg tablet Disp Pack35.99USD disp
Ortho-Novum 7/7/7 (28) 28 0.5/0.75/1-35 mg-mcg tablet Disp Pack33.99USD disp
Necon 0.5/35 (28) 28 0.5-35 mg-mcg tablet Disp Pack32.99USD disp
Necon 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack31.99USD disp
Loestrin fe 1-20 tablet5.23USD tablet
Loestrin 21 1.5-30 tablet3.66USD tablet
Loestrin 21 1-20 tablet3.66USD tablet
Aygestin 5 mg tablet3.27USD tablet
Ovcon-35 28 tablet3.06USD tablet
Loestrin fe 1.5-30 tablet2.75USD tablet
Norethindrone Acetate 5 mg tablet2.75USD tablet
Norethindrone 5 mg tablet2.65USD tablet
Ovcon-50 28 tablet2.62USD tablet
Micronor tablet2.44USD tablet
Nor-q-d tablet2.24USD tablet
Necon 1-35-28 tablet2.11USD tablet
Modicon 28 tablet2.07USD tablet
Tri-norinyl 28 tablet2.01USD tablet
Ortho-novum 1-35-28 tablet1.9USD tablet
Brevicon 28 tablet1.8USD tablet
Norinyl 1+35-28 tablet1.73USD tablet
Norinyl 1+50-28 tablet1.73USD tablet
Demulen 1-50-21 tablet1.67USD tablet
Ortho-novum 7-7-7-21 tablet1.4USD tablet
Errin 0.35 mg tablet1.34USD tablet
Ortho-novum 7/7/7-28 tablet1.33USD tablet
Camila tablet1.32USD tablet
Jolivette tablet1.32USD tablet
Nora-be tablet1.32USD tablet
Norethindrone 0.35 mg tablet1.32USD tablet
Demulen 1-50-28 tablet1.29USD tablet
Ortho micronor tablet1.23USD tablet
Necon 0.5-35-28 tablet1.15USD tablet
Necon 7-7-7-28 tablet1.15USD tablet
Necon 1-50-28 tablet1.05USD tablet
Ortho-novum 7-7-7-28 tablet1.02USD tablet
Micronor (28 Day) 0.35 mg Tablet0.66USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6036976No2000-03-142016-12-13Us
US6667050No2003-12-232019-04-06Us
US7704984No2010-04-272029-02-02Us
US6652880No2003-11-252020-03-29Us
Additional Data Available
  • Filed On
    Filed On

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)203.5 °CPhysProp
water solubility7.04 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.97HANSCH,C ET AL. (1995)
logS-4.57ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.00668 mg/mLALOGPS
logP2.72ALOGPS
logP3.22ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.42 m3·mol-1ChemAxon
Polarizability34.59 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9413
Caco-2 permeable+0.8572
P-glycoprotein substrateSubstrate0.6346
P-glycoprotein inhibitor IInhibitor0.5079
P-glycoprotein inhibitor IINon-inhibitor0.9087
Renal organic cation transporterNon-inhibitor0.7603
CYP450 2C9 substrateNon-substrate0.7759
CYP450 2D6 substrateNon-substrate0.9237
CYP450 3A4 substrateSubstrate0.7415
CYP450 1A2 substrateNon-inhibitor0.844
CYP450 2C9 inhibitorNon-inhibitor0.8688
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8333
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7876
Ames testNon AMES toxic0.9319
CarcinogenicityNon-carcinogens0.9417
BiodegradationNot ready biodegradable0.9512
Rat acute toxicity1.8788 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8777
hERG inhibition (predictor II)Non-inhibitor0.7744
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-01rt-4950000000-fcbe8bf03b1aa103152b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a5c-3900000000-4b2a5d95e4b6d50f16fc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00ea-0790000000-60d1a1a37c0ba98d6a4a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00e9-0890000000-5d3b8210450a1c43b119
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0391000000-ae51cc90bb8f2161f149
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ar0-3920000000-e31fa7c9e871f2e39846
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Delta-4-steroid / Cyclohexenone / Ynone / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, tertiary alcohol, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:7627) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05028) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030097)

Targets

Details
1. Progesterone receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Mendoza-Rodriguez CA, Camacho-Arroyo I, Garcia GA, Cerbon MA: Variations of progesterone receptor and c-fos gene expression in the rat uterus after treatment with norethisterone and its A-ring reduced metabolites. Contraception. 1999 May;59(5):339-43. [PubMed:10494488]
  2. Madauss KP, Deng SJ, Austin RJ, Lambert MH, McLay I, Pritchard J, Short SA, Stewart EL, Uings IJ, Williams SP: Progesterone receptor ligand binding pocket flexibility: crystal structures of the norethindrone and mometasone furoate complexes. J Med Chem. 2004 Jun 17;47(13):3381-7. [PubMed:15189034]
  3. Garcia-Becerra R, Cooney AJ, Borja-Cacho E, Lemus AE, Perez-Palacios G, Larrea F: Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins. J Steroid Biochem Mol Biol. 2004 Jun;91(1-2):21-7. [PubMed:15261304]
  4. Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894]
  5. Pasapera AM, Cerbon MA, Castro I, Gutierrez R, Camacho-Arroyo I, Garcia GA, Perez-Palacios G: Norethisterone metabolites modulate the uteroglobin and progesterone receptor gene expression in prepubertal rabbits. Biol Reprod. 1995 Feb;52(2):426-32. [PubMed:7711211]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...

Components:
References
  1. Hall SD, Wang Z, Huang SM, Hamman MA, Vasavada N, Adigun AQ, Hilligoss JK, Miller M, Gorski JC: The interaction between St John's wort and an oral contraceptive. Clin Pharmacol Ther. 2003 Dec;74(6):525-35. doi: 10.1016/j.clpt.2003.08.009. [PubMed:14663455]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2019 10:27