Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C59H84N16O12.C2H4O2 |
Molecular Weight | 1269.4502 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=C3C=CC=C4)NC(=O)[C@H](CC5=CNC=N5)NC(=O)[C@@H]6CCC(=O)N6
InChI
InChIKey=RGLRXNKKBLIBQS-XNHQSDQCSA-N
InChI=1S/C59H84N16O12.C2H4O2/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40;1-2(3)4/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64);1H3,(H,3,4)/t40-,41-,42-,43+,44-,45-,46-,47-,48-;/m0./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/7533699Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/ppa/leuprolide.html | http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020011s040lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019010s033,019732s031s035s036,020517s024s028s029lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7533699
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/ppa/leuprolide.html | http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020011s040lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019010s033,019732s031s035s036,020517s024s028s029lbl.pdf
Leuprolide acetate is a synthetic nonapeptide analog of naturally occurring gonadotropin-releasing hormone (GnRH or LH-RH). The analog possesses greater potency than the natural hormone. It acts primarily on the anterior pituitary, inducing a transient early rise in gonadotrophin release. With continued use, leuprorelin causes pituitary desensitisation and/or down-regulation, leading to suppressed circulating levels of gonadotrophins and sex hormones. Leuprolide acetate used to treat a wide range of sex hormone-related disorders including advanced prostatic cancer, uterine leiomyomata (fibroids), endometriosis and precocious puberty.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7533699 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | LUPRON Approved UseLEUPROLIDE ACETATE INJECTION is indicated in the palliative treatment of advanced prostatic cancer. Launch Date1985 |
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Primary | LUPRON DEPOT Approved UseEndometriosis
LUPRON DEPOT 3.75 mg is indicated for management of endometriosis, including pain relief and reduction of endometriotic lesions. LUPRON DEPOT monthly with norethindrone acetate 5 mg daily is also indicated for initial management of endometriosis and for management of recurrence of symptoms. (Refer also to
norethindrone acetate prescribing information for WARNINGS, PRECAUTIONS, CONTRAINDICATIONS and ADVERSE REACTIONS associated with norethindrone acetate). Duration of initial treatment or retreatment should be limited to 6 months.
Uterine Leiomyomata (Fibroids)
LUPRON DEPOT 3.75 mg concomitantly with iron therapy is indicated for the preoperative hematologic improvement of patients with anemia caused by uterine leiomyomata. The clinician may wish to consider a one-month trial period on iron alone inasmuch as some of the patients will respond to iron alone. (See Table
1.) LUPRON may be added if the response to iron alone is considered inadequate. Recommended duration of therapy with LUPRON DEPOT 3.75 mg is up to three months. Experience with LUPRON DEPOT in females has been limited to women 18 years of age and older. Launch Date1995 |
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Primary | LUPRON DEPOT Approved UseEndometriosis
LUPRON DEPOT 3.75 mg is indicated for management of endometriosis, including pain relief and reduction of endometriotic lesions. LUPRON DEPOT monthly with norethindrone acetate 5 mg daily is also indicated for initial management of endometriosis and for management of recurrence of symptoms. (Refer also to
norethindrone acetate prescribing information for WARNINGS, PRECAUTIONS, CONTRAINDICATIONS and ADVERSE REACTIONS associated with norethindrone acetate). Duration of initial treatment or retreatment should be limited to 6 months.
Uterine Leiomyomata (Fibroids)
LUPRON DEPOT 3.75 mg concomitantly with iron therapy is indicated for the preoperative hematologic improvement of patients with anemia caused by uterine leiomyomata. The clinician may wish to consider a one-month trial period on iron alone inasmuch as some of the patients will respond to iron alone. (See Table
1.) LUPRON may be added if the response to iron alone is considered inadequate. Recommended duration of therapy with LUPRON DEPOT 3.75 mg is up to three months. Experience with LUPRON DEPOT in females has been limited to women 18 years of age and older. Launch Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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32.48 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27824264 |
11.25 mg single, subcutaneous dose: 11.25 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
LEUPROLIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
426.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27824264 |
11.25 mg single, subcutaneous dose: 11.25 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
LEUPROLIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 h |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEUPROLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54% |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEUPROLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Other AEs: Asthenia, General body pain... Other AEs: Asthenia (6 patients) Sources: General body pain (16 patients) Headache (5 patients) Injection site reaction (4 patients) Hot flashes (23 patients) Gastrointestinal disorder (NOS) (5 patients) Dehydration (4 patients) Edema (4 patients) Disorder joint (8 patients) Myalgia (4 patients) Vertigo (3 patients) Neuromuscular disorders (3 patients) Paresthesia (4 patients) Skin reaction (6 patients) Urinary tract disorder NOS (5 patients) |
7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Other AEs: General body pain, Hot flashes... Other AEs: General body pain (13 patients) Sources: Hot flashes (32 patients) Gastrointestinal disorder (NOS) (8 patients) Edema (8 patients) Libido decreased (3 patients) Disorder urinary tract (7 patients) Impotence (3 patients) Atrophy testicular (3 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
General body pain | 16 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Hot flashes | 23 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Neuromuscular disorders | 3 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Vertigo | 3 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Dehydration | 4 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Edema | 4 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Injection site reaction | 4 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Myalgia | 4 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Paresthesia | 4 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Gastrointestinal disorder (NOS) | 5 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Headache | 5 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Urinary tract disorder NOS | 5 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Asthenia | 6 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Skin reaction | 6 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
Disorder joint | 8 patients | 30 mg 1 times / month multiple, subcutaneous Highest studied dose Dose: 30 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / month Sources: |
unhealthy, adult n = 49 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 49 Sources: |
General body pain | 13 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Atrophy testicular | 3 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Impotence | 3 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Libido decreased | 3 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Hot flashes | 32 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Disorder urinary tract | 7 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Edema | 8 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
Gastrointestinal disorder (NOS) | 8 patients | 7.5 mg 1 times / month multiple, subcutaneous Recommended Dose: 7.5 mg, 1 times / month Route: subcutaneous Route: multiple Dose: 7.5 mg, 1 times / month Sources: |
unhealthy, adult n = 56 Health Status: unhealthy Condition: cancer Age Group: adult Sex: unknown Population Size: 56 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Stable transfection of GH3 cells with rat gonadotropin-releasing hormone receptor complementary deoxyribonucleic acid results in expression of a receptor coupled to cyclic adenosine 3',5'-monophosphate-dependent prolactin release via a G-protein. | 1994 Jul |
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[Effects of androgen regulation system on bladder carcinogenesis in male mice]. | 1995 Nov |
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Pituitary apoplexy after leuprolide administration for carcinoma of the prostate. | 1996 Jan |
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"Add-back" estrogen reverses cognitive deficits induced by a gonadotropin-releasing hormone agonist in women with leiomyomata uteri. | 1996 Jul |
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Anxiety and mood disorders associated with gonadotropin-releasing hormone agonist therapy. | 1997 |
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Pituitary apoplexy of a gonadotroph adenoma following gonadotrophin releasing hormone agonist therapy for prostatic cancer. | 1997 Oct |
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Steroidal 'add-back' therapy in patients treated with GnRH agonists. | 1998 |
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Sertraline in the treatment of depression associated with gonadotropin-releasing hormone agonist therapy. | 1998 Mar 15 |
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Lupron-induced mania. | 1999 Jan 15 |
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Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs. | 1999 Mar |
|
Altered cognitive function in men treated for prostate cancer with luteinizing hormone-releasing hormone analogues and cyproterone acetate: a randomized controlled trial. | 2002 Sep |
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Combined androgen blockade-induced anemia in prostate cancer patients without bone involvement. | 2003 Mar-Apr |
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Pituitary apoplexy after leuprolide. | 2006 |
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Gonadotropin-releasing hormone agonists reduce the migratory and the invasive behavior of androgen-independent prostate cancer cells by interfering with the activity of IGF-I. | 2007 Jan |
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[Ischemic stroke associated with LH-RH analogue (leuprorelin) administration in a young woman]. | 2007 May |
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A possible participation of gonadotropin-releasing hormone in the neuroleptic and cataleptic effect of haloperidol. | 2009 Jun |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/leuprolide.html
Dosing: Adult
Prostate cancer, advanced: Note: Treatment is usually continued after development of metastatic (castration-resistant) disease.
IM:
Lupron Depot 7.5 mg (monthly): 7.5 mg every month or
Lupron Depot 22.5 mg (3 month): 22.5 mg every 12 weeks or
Lupron Depot 30 mg (4 month): 30 mg every 16 weeks or
Lupron Depot 45 mg (6 month): 45 mg every 24 weeks
SubQ:
Eligard: 7.5 mg monthly or 22.5 mg every 3 months or 30 mg every 4 months or 45 mg every 6 months
Leuprolide acetate 5 mg/mL solution: 1 mg daily
Endometriosis: IM: Initial therapy may be with leuprolide alone or in combination with norethindrone; if re-treatment for an additional 6 months is necessary, concomitant norethindrone should be used. Re-treatment is not recommended for longer than one additional 6-month course.
Lupron Depot: 3.75 mg every month for up to 6 months or
Lupron Depot-3 month: 11.25 mg every 3 months for up to 2 doses (6 months total duration of treatment)
Uterine leiomyomata (fibroids): IM (in combination with iron):
Lupron Depot: 3.75 mg every month for up to 3 months or
Lupron Depot-3 month: 11.25 mg as a single injection
Breast cancer, premenopausal ovarian supression (off-label use): IM:
Lupron Depot: 3.75 mg every 28 days for up to 24 months (Boccardo 1999) or
Lupron Depot-3 month: 11.25 mg every 3 months for up to 24 months (Boccardo 1999; Schmid 2007)
Treatment of paraphilia/hypersexuality (off-label use; Guay 2009; Reilly 2000): Males: IM:
Note: May cause an initial increase in androgen concentrations which may be treated with an antiandrogen (eg, flutamide, cyproterone) for 1 to 2 months (Guay 2009). Avoid use in patients with osteoporosis or active pituitary pathology.
SubQ: Test dose: 1 mg (observe for hypersensitivity)
Depot IM: 3.75 to 7.5 mg monthly
Dosing: Geriatric
Refer to adult dosing.
Dosing: Pediatric
Precocious puberty (consider discontinuing by age 11 for females and by age 12 for males):
IM:
Lupron Depot-Ped (monthly):
≤25 kg: 7.5 mg every month
>25 to 37.5 kg: 11.25 mg every month
>37.5 kg: 15 mg every month
Titrate dose upward in increments of 3.75 mg every 4 weeks if down-regulation is not achieved.
Lupron Depot-Ped (3 month): 11.25 mg or 30 mg every 12 weeks
SubQ (leuprolide acetate 5 mg/mL solution): Initial: 50 mcg/kg/day; titrate dose upward by 10 mcg/kg/day if down-regulation is not achieved. Note: Higher mg/kg doses may be required in younger children.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16809153
In primary cell cultures from human prostate carcinoma leuprolide (from 5-20 ng/mL) showed a significant reduction in cell growth rate and an increase in DNA-fragmented cell number.
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/16/1821
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FDA ORPHAN DRUG |
28688
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NCI_THESAURUS |
C1910
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203217
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CHEMBL1201199
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37JNS02E7V
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SUB02900MIG
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DBSALT000105
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m6779
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C1319
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100000091573
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88793-81-1
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NON-SPECIFIC STOICHIOMETRY | |||
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DTXSID7049009
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37JNS02E7V
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657180
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63597
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74381-53-6
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1358503
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ACTIVE MOIETY
SUBSTANCE RECORD