Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H28O3 |
Molecular Weight | 340.4559 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]
InChI
InChIKey=IMONTRJLAWHYGT-ZCPXKWAGSA-N
InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8520623
https://www.medicines.org.uk/emcmobile/PIL.23891.latest.pdf
http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018405s023lbl.pdf
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8520623
https://www.medicines.org.uk/emcmobile/PIL.23891.latest.pdf
http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018405s023lbl.pdf
Norethisterone (INN, BAN), also known as Norethindrone (USAN) (brand names Micronor, AYGESTIN, numerous others) is a synthetic progestational hormone (progestin) 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 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. AYGESTIN® is not intended, recommended or approved to be used with oncomitant estrogen therapy in postmenopausal women for endometrial protection. 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. Allergic reaction could be: Itching or hives, swelling in your face or hands, swelling or tingling in your mouth or throat, chest tightness, trouble breathing.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6319907
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Norethindrone affects the levels of opioid petides in the rat brain, but it is not clear whether this action is mediated by direct activity within CNS
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189034 |
6.8 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | MICRONOR Approved UseIndications Progestin-only oral contraceptives are indicated for the prevention of pregnancy. 2. Efficacy If used perfectly, the first-year failure rate for progestin-only oral contraceptives is 0.5%. However, the typical failure rate is estimated to be closer to 5%, due to late or omitted pills. Table 1 lists the pregnancy rates for users of all major methods of contraception. Table 1: Percentage of Women Experiencing an Unintended Pregnancy During the First Year of Typical Use and the First Year of Perfect Use of Contraception and the Percentage Continuing Use at the End of the First Year. United States. Adapted from Hatcher et al, 1998, Ref. #1 Emergency Contraceptive Pills: Treatment initiated within 72 hours after unprotected intercourse reduces the risk of pregnancy by at least 75%The treatment schedule is one dose within 72 hours after unprotected intercourse, and a second dose 12 hours after the first dose. The Food and Drug Administration has declared the following brands of oral contraceptives to be safe and effective for emergency contraception: Ovral® (1 dose is 2 white pills), Alesse® (1 dose is 5 pink pills), Nordette® or Levlen® (1 dose is 2 light-orange pills), Lo/Ovral® (1 dose is 4 white pills), Triphasil ® or Tri-Levlen® (1 dose is 4 yellow pills) Lactational Amenorrhea Method: LAM is highly effective, temporary method of contraceptionHowever, to maintain effective protection against pregnancy, another method of contraception must be used as soon as menstruation resumes, the frequency or duration of breastfeeds is reduced, bottle feeds are introduced, or the baby reaches six months of age. Source: Trussell J, Contraceptive efficacy. In Hatcher RA, Trussel J, Stewart F, Cates W, Stewart GK, Kowal D, Guest F, Contraceptive Technology: Seventeenth Revised Edition. New York NY: Irvington Publishers, 1998. % of Women Experiencing an Unintended Pregnancy within the First Year of Use % of Women Continuing Use at One Year Among couples attempting to avoid pregnancy, the percentage who continue to use a method for one year Method (1) Typical UseAmong typical couples who initiate use of a method (not necessarily for the first time), the percentage who experience an accidental pregnancy during the first year if they do not stop use for any other reason (2) Perfect UseAmong couples who initiate use of a method (not necessarily for the first time) and who use it perfectly (both consistently and correctly), the percentage who experience an accidental pregnancy during the first year if they do not stop use for any other reason (3) (4) ChanceThe percents becoming pregnant in columns (2) and (3) are based on data from populations where contraception is not used and from women who cease using contraception in order to become pregnant. Among such populations, about 89% become pregnant within one year. This estimate was lowered slightly (to 85%) to represent the percent who would become pregnant within one year among women now relying on reversible methods of contraception if they abandoned contraception altogether 85 85 SpermicidesFoams, creams, gels, vaginal suppositories, and vaginal film 26 6 40 Periodic abstinence 25 63 Calendar 9 Ovulation Method 3 Sympto-Thermal Cervical mucus (ovulation) method supplemented by calendar in the pre-ovulatory and basal body temperature in the post-ovulatory phases 2 Post-Ovulation 1 CapWith spermicidal cream or jelly Parous Women 40 26 42 Nulliparous Women 20 9 56 Sponge Parous Women 40 20 42 Nulliparous Women 20 9 56 Diaphragm 20 6 56 Withdrawal 19 4 CondomWithout spermicides Female (Reality®) 21 5 56 Male 14 3 61 Pill 5 71 Progestin Only 0.5 Combined 0.1 IUD Progesterone T 2.0 1.5 81 Copper T380A 0.8 0.6 78 LNg 20 0.1 0.1 81 Depo-Provera® 0.3 0.3 70 Norplant® and Norplant-2® 0.05 0.05 88 Female Sterilization 0.5 0.5 100 Male Sterilization 0.15 0.10 100 Norethindrone tablets have not been studied for and are not indicated for use in emergency contraception. Launch Date9.4780801E10 |
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Primary | AYGESTIN Approved UseAYGESTIN® is indicated 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. AYGESTIN® is not intended, recommended or approved to be used with concomitant estrogen therapy in postmenopausal women for endometrial protection. Launch Date3.88108812E11 |
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Primary | AYGESTIN Approved UseAYGESTIN® is indicated 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. AYGESTIN® is not intended, recommended or approved to be used with concomitant estrogen therapy in postmenopausal women for endometrial protection. Launch Date3.88108812E11 |
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Primary | AYGESTIN Approved UseAYGESTIN® is indicated 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. AYGESTIN® is not intended, recommended or approved to be used with concomitant estrogen therapy in postmenopausal women for endometrial protection. Launch Date3.88108812E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26.19 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORETHINDRONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
166.9 ng × h/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORETHINDRONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.51 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORETHINDRONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORETHINDRONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
15 mg 1 times / day multiple, oral Studied dose Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, 10.2-41.9 years Health Status: unhealthy Condition: Endometriosis Age Group: 10.2-41.9 years Sex: F Sources: |
Other AEs: Weight gain... |
20 uCi single, intravenous Dose: 20 uCi Route: intravenous Route: single Dose: 20 uCi Sources: |
healthy, 25-35 years n = 6 Health Status: healthy Age Group: 25-35 years Sex: F Population Size: 6 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Weight gain | 15 mg 1 times / day multiple, oral Studied dose Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, 10.2-41.9 years Health Status: unhealthy Condition: Endometriosis Age Group: 10.2-41.9 years Sex: F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 9.0 |
weak [IC50 46 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/ Page: 1.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 2.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18356043/ Page: 2.0 |
yes | |||
Sources: https://hmdb.ca/metabolites/HMDB0014855 |
yes | |||
Sources: https://hmdb.ca/metabolites/HMDB0014855 |
yes | |||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[A clinical assessment of a 3 month replacement therapy effectiveness with low norethisterone acetate (Activelle) in postmenopausal women]. | 2001 |
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The effect of medroxyprogesterone acetate and norethisterone on the estradiol stimulated proliferation in MCF-7 cells: comparison of continuous combined versus sequential combined estradiol/progestin treatment. | 2001 |
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[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects]. | 2001 |
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Biphasic versus triphasic oral contraceptives for contraception. | 2001 |
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Biphasic versus monophasic oral contraceptives for contraception. | 2001 |
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Bone-resorbing cytokines from peripheral blood mononuclear cells after hormone replacement therapy: a longitudinal study. | 2001 |
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Detection of estrogenicity by bioassay on the mouse mammary gland in vivo. | 2001 |
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Effects of 17 beta-estradiol and trimegestone alone, and in combination, on the bone and uterus of ovariectomized rats. | 2001 Aug |
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Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. | 2001 Aug |
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Evaluation of interaction between fluconazole and an oral contraceptive in healthy women. | 2001 Aug |
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Pharmacology and toxicology of ethinyl estradiol and norethindrone acetate in experimental animals. | 2001 Aug |
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Comparison between 1 year oral and transdermal oestradiol and sequential norethisterone acetate on circulating concentrations of leptin in postmenopausal women. | 2001 Aug |
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Effects of hormone replacement therapy and high-impact physical exercise on skeletal muscle in post-menopausal women: a randomized placebo-controlled study. | 2001 Aug |
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Heparan sulfate mimetics modulate calpain activity during rat Soleus muscle regeneration. | 2001 Aug |
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Omental pregnancy in a woman taking the progestogen-only pill. | 2001 Dec |
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Acceptability and patterns of endometrial bleeding in estradiol-based HRT regimens: a comparative study of cyclical sequential combinations of trimegestone or norethisterone acetate. | 2001 Dec |
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Differential effects of raloxifene and continuous combined hormone replacement therapy on biochemical markers of cardiovascular risk: results from the Euralox 1 study. | 2001 Dec |
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The effects of postmenopausal hormone replacement therapy and oral contraceptives on the endogenous estradiol metabolism. | 2001 Dec |
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The effect of continuous combined hormone replacement therapy on arterial reactivity in postmenopausal women with established angina pectoris. | 2001 Dec |
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Glycaemic control and plasma lipoproteins in menopausal women with Type 2 diabetes treated with oral and transdermal combined hormone replacement therapy. | 2001 Dec |
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Use of solid-phase extraction in various of its modalities for sample preparation in the determination of estrogens and progestogens in sediment and water. | 2001 Dec 14 |
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Fine structure of prolactin cell of female albino rat as affected by some antifertility drugs--a comparative electron microscopic study. | 2001 Feb |
|
Comparison of a novel norgestimate/ethinyl estradiol oral contraceptive (Ortho Tri-Cyclen Lo) with the oral contraceptive Loestrin Fe 1/20. | 2001 Jun |
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[Effect of tibolone on vascular markers of human female coronary arteries - comparison with estradiol/norethisterone]. | 2001 Nov |
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Effects of oral and transdermal hormone replacement therapy on internal carotid artery pulsatility indices in postmenopausal women. A prospective, randomized, comparative study. | 2001 Nov |
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Drug interactions between oral contraceptives and antibiotics. | 2001 Nov |
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Hormone replacement therapy and acquired resistance to activated protein C: results of a randomized, double-blind, placebo-controlled trial. | 2001 Nov |
|
A multicenter, randomized, clinical trial of hormonal therapy in the prevention of rebleeding from gastrointestinal angiodysplasia. | 2001 Nov |
|
Solution structure and backbone dynamics of an engineered arginine-rich subdomain 2 of the hepatitis C virus NS3 RNA helicase. | 2001 Nov 30 |
|
Monitoring of solid-phase organic synthesis on macroscopic supports by high-resolution magic angle spinning NMR. | 2001 Nov-Dec |
|
Impact of oral contraceptive use on APC-resistance: a prospective, randomized clinical trial with three low-dose preparations. | 2001 Oct |
|
Obesity and sarcopenia after menopause are reversed by sex hormone replacement therapy. | 2001 Oct |
|
A longitudinal study of disturbances of the hypothalamic-pituitary-adrenal axis in women with progestin-negative functional hypothalamic amenorrhea. | 2001 Oct |
|
A prospective, controlled study of the effects of hormonal contraception on bone mineral density. | 2001 Oct |
|
Effects of HRT on serum levels of IGF-I in postmenopausal women. | 2001 Oct 31 |
|
[Cross-over comparison of the pharmacokinetics of estradiol during hormone replacement therapy with estradiol valerate or micronized estradiol]. | 2001 Sep |
|
Bone densitometry in clinical practice: longitudinal measurements at three sites in postmenopausal women on five treatments. | 2001 Sep |
|
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women. | 2001 Sep |
|
Effect of conjugated estrogens on free IGF-I? | 2001 Sep |
|
Influence of postmenopausal hormone replacement therapy on platelet serotonin uptake site and serotonin 2A receptor binding. | 2001 Sep |
|
A-ring reduced metabolites of 19-nor synthetic progestins as subtype selective agonists for ER alpha. | 2001 Sep |
|
Progesterone and norethisterone have different effects on tachykinin-like immunoreactivity in rat cortex and striatum. | 2001 Sep 15 |
|
Unscheduled bleeding during initiation of continuous combined hormone replacement therapy: a direct comparison of two combinations of norethindrone acetate and ethinyl estradiol to medroxyprogesterone acetate and conjugated equine estrogens. | 2001 Sep-Oct |
|
Effect of rofecoxib on the pharmacokinetics of chronically administered oral contraceptives in healthy female volunteers. | 2002 Feb |
|
Hormone replacement therapy can augment vascular relaxation in post-menopausal women with type 2 diabetes. | 2002 Feb |
|
The efficacy of two dosages of a continuous combined hormone replacement regimen. | 2002 Feb 26 |
|
Triphasic oral contraceptives: review and comparison of various regimens. | 2002 Jan |
|
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals. | 2002 Jan 15 |
|
Does postmenopausal hormone replacement therapy affect cardiac autonomic regulation in osteoporotic women? | 2002 Jan-Feb |
|
Postmenopausal uterine bleeding profiles with two forms of continuous combined hormone replacement therapy. | 2002 Jan-Feb |
Sample Use Guides
Secondary amenorrhea, abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology: 2.5 to 10 mg may be given daily for 5 to 10 days to produce secretory transformation of an endometrium that has been adequately primed with either endogenous or exogenous estrogen.
Endometriosis: Initial daily dosage of 5 mg for two weeks. Dosage should be increased by 2.5 mg per day every two weeks until 15 mg per day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1834933
Curator's Comment: Growth of MCF-7 cells was stimulated by norethindrone (10(-8)-10(-5) M), with maximal growth stimulation at 10(-7) M norethindrone after 7 days of treatment
10 - 10000 nM norethindrone stimulates growth of MCF-7 cells
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C776
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Code System | Code | Type | Description | ||
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C702
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m8056
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PRIMARY | Merck Index | ||
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C024262
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1470004
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5832
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9S44LIC7OJ
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9S44LIC7OJ
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1963
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NORETHINDRONE ACETATE
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PRIMARY | Description: A white or creamy white, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 12.5 parts of ethanol (~750 g/l) TS and in 4 parts of acetone R; sparinglysoluble in ether R. Category: Progestational steroid. Storage: Norethisterone acetate should be kept in a well-closed container, protected from light. Definition: Norethisterone acetate contains not less than 97.0% and not more than 103.0% of C22H28O3, calculated withreference to the dried substance. | ||
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CHEMBL1201146
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100000093036
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200-132-0
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NORETHISTERONE ACETATE
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SUB03457MIG
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22844
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51-98-9
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31983
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DBSALT000129
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7628
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DTXSID4023381
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ACTIVE MOIETY
SUBSTANCE RECORD