Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H21N |
| Molecular Weight | 167.2916 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@@]2([H])CC[C@]([H])(C2)[C@]1(C)NC
InChI
InChIKey=IMYZQPCYWPFTAG-NGZCFLSTSA-N
InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3/t8-,9+,11-/m0/s1
| Molecular Formula | C11H21N |
| Molecular Weight | 167.2916 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Mecamylamine (Inversine), the first orally available
antihypertensive agent, is now rarely used. Introduced as a therapeutic agent
for the treatment of hypertension in the 1950s,
mecamylamine was the first useful ganglionic blocking
agent that was not a quarternary ammonium
compound. Mecamylamine is indicated for the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Mecamylamine reduces blood pressure in both normotensive and hypertensive individuals. A small oral dosage often produces a smooth and predictable reduction of blood pressure. Although this antihypertensive effect is predominantly orthostatic, the supine blood pressure is also significantly reduced. Mecamylamine is a nicotinic parasympathetic ganglionic blocker. Mecamylamine administration produces several deleterious side-effects at therapeutically relevant doses. As such, mecamylamine’s use as an antihypertensive agent was phased out, except in severe hypertension. Mecamylamine easily traverses the blood-brain barrier to reach the central nervous system (CNS), where it acts as a nicotinic acetylcholine receptor (nAChR) antagonist, inhibiting all known nAChR subtypes. Since nAChRs play a major role in numerous physiological and pathological processes, it is not surprising that mecamylamine has been evaluated for its potential therapeutic effects in a wide variety of CNS disorders, including addiction.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.6 µM [Ki] | |||
Target ID: CHEMBL1907589 |
2.5 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | INVERSINE Approved UseFor the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Launch Date-4.36665614E11 |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
23.68 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
115.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
352.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
149.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
467.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
150.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
472.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389 |
7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECAMYLAMINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
Other AEs: Nausea, Somnolence... Other AEs: Nausea (10.3%) Sources: Somnolence (34.5%) Dizziness (17.2%) Fatigue (24.1%) Orthostatic hypotension (27.6%) Headache (10.3%) Application site pruritus (3.4%) Vision blurred (17.2%) Constipation (13.8%) Vomiting (3.4%) Dizziness postural (3.4%) Abdominal pain (10.3%) Abdominal distension (3.4%) |
5 mg 2 times / day multiple, oral Recommended Dose: 5 mg, 2 times / day Route: oral Route: multiple Dose: 5 mg, 2 times / day Sources: |
healthy, mean age 34.1 years n = 24 Health Status: healthy Age Group: mean age 34.1 years Sex: M+F Population Size: 24 Sources: |
DLT: Abdominal pain, Constipation... Dose limiting toxicities: Abdominal pain (4.2%) Sources: Constipation (4.2%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abdominal pain | 10.3% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Headache | 10.3% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Nausea | 10.3% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Constipation | 13.8% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Dizziness | 17.2% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Vision blurred | 17.2% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Fatigue | 24.1% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Orthostatic hypotension | 27.6% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Abdominal distension | 3.4% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Application site pruritus | 3.4% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Dizziness postural | 3.4% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Vomiting | 3.4% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Somnolence | 34.5% | 30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: |
healthy, 18 -45 years n = 29 Health Status: healthy Age Group: 18 -45 years Sex: M Population Size: 29 Sources: |
| Abdominal pain | 4.2% DLT |
5 mg 2 times / day multiple, oral Recommended Dose: 5 mg, 2 times / day Route: oral Route: multiple Dose: 5 mg, 2 times / day Sources: |
healthy, mean age 34.1 years n = 24 Health Status: healthy Age Group: mean age 34.1 years Sex: M+F Population Size: 24 Sources: |
| Constipation | 4.2% DLT |
5 mg 2 times / day multiple, oral Recommended Dose: 5 mg, 2 times / day Route: oral Route: multiple Dose: 5 mg, 2 times / day Sources: |
healthy, mean age 34.1 years n = 24 Health Status: healthy Age Group: mean age 34.1 years Sex: M+F Population Size: 24 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of cholingeric drugs on methadone-induced catalepsy and stereotypies in rats treated chronically with methadone. | 1976 Oct |
|
| Nicotine-sensitive paresis. | 1992 Feb |
|
| [Assessment of anti-tremorogenic drugs--nicotine-induced tail-tremor model]. | 1997 Jun |
|
| Role of central nicotinic and beta-adrenergic receptors in the onset and further development of tail-tremor induced by repeated nicotine administration to rats. | 1997 May |
|
| Nicotine potentiates sulpiride-induced catalepsy in mice. | 1998 |
|
| Rat alpha3/beta4 subtype of neuronal nicotinic acetylcholine receptor stably expressed in a transfected cell line: pharmacology of ligand binding and function. | 1998 Aug |
|
| Nicotine prevents experimental parkinsonism in rodents and induces striatal increase of neurotrophic factors. | 1998 Dec |
|
| Anti-nicotinic properties of anticholinergic antiparkinson drugs. | 1998 Nov |
|
| Pharmacological characterization of nicotine-induced seizures in mice. | 1999 Dec |
|
| Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant. | 1999 Feb 5 |
|
| Sex differences in cholinergic analgesia II: differing mechanisms in two models of allodynia. | 1999 Nov |
|
| Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats. | 2000 Apr |
|
| Chronic nicotine exposure reduces N-methyl-D-aspartate receptor-mediated damage in the hippocampus without altering calcium accumulation or extrusion: evidence of calbindin-D28K overexpression. | 2001 |
|
| Mecamylamine effects on haloperidol-induced catalepsy and defecation. | 2001 Jul |
|
| Nicotine induced seizures blocked by mecamylamine and its stereoisomers. | 2001 Oct 19 |
|
| DM235 (sunifiram): a novel nootropic with potential as a cognitive enhancer. | 2002 Jun |
|
| Nicotine potentiation of morphine-induced catalepsy in mice. | 2002 May |
|
| Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. | 2003 Dec |
|
| Castration in rats impairs performance during acquisition of a working memory task and exacerbates deficits in working memory produced by scopolamine and mecamylamine. | 2003 Nov |
|
| Nicotine attenuates beta-amyloid peptide-induced neurotoxicity, free radical and calcium accumulation in hippocampal neuronal cultures. | 2004 Feb |
|
| Tolerance to pentylentetrazol-induced convulsions and protection of cerebrovascular integrity by chronic nicotine. | 2004 Jun |
|
| Nicotine attenuates oxidative stress, activation of redox-regulated transcription factors and induction of proinflammatory genes in compressive spinal cord trauma. | 2004 May 19 |
|
| Decreased signs of nicotine withdrawal in mice null for the beta4 nicotinic acetylcholine receptor subunit. | 2004 Nov 10 |
|
| Nicotine-induced antinociception, rewarding effects, and physical dependence are decreased in mice lacking the preproenkephalin gene. | 2005 Feb 2 |
|
| Enhancement of PAI-1 mRNA in cardiovascular cells after kainate injection is mediated through the sympathetic nervous system. | 2005 May |
|
| Active immunisation against nicotine blocks the reward facilitating effects of nicotine and partially prevents nicotine withdrawal in the rat as measured by dopamine output in the nucleus accumbens, brain reward thresholds and somatic signs. | 2005 Nov |
|
| Naloxone precipitates nicotine abstinence syndrome and attenuates nicotine-induced antinociception in mice. | 2005 Nov-Dec |
|
| Untranslated region-dependent exclusive expression of high-sensitivity subforms of alpha4beta2 and alpha3beta2 nicotinic acetylcholine receptors. | 2006 Jul |
|
| Nicotine attenuates beta-amyloid-induced neurotoxicity by regulating metal homeostasis. | 2006 Jun |
|
| Nicotinic receptors mediate tumorigenic action of tobacco-derived nitrosamines on immortalized oral epithelial cells. | 2006 May |
|
| The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells. | 2006 Oct |
|
| Nicotinic modulation of gene expression in SH-SY5Y neuroblastoma cells. | 2006 Oct 20 |
|
| The involvement of the central cholinergic system in the pressor and bradycardic effects of centrally administrated melittin in normotensive conscious rats. | 2007 Apr |
|
| Nicotine-induced dystonic arousal complex in a mouse line harboring a human autosomal-dominant nocturnal frontal lobe epilepsy mutation. | 2007 Sep 19 |
|
| Glutamatergic contributions to nicotinic acetylcholine receptor agonist-evoked cholinergic transients in the prefrontal cortex. | 2008 Apr 2 |
|
| Nicotinic signaling ameliorates acute bladder inflammation induced by protamine sulfate or cyclophosphamide. | 2008 Jun |
|
| Mecamylamine prevents neuronal apoptosis induced by glutamate and low potassium via differential anticholinergic-independent mechanisms. | 2008 Mar |
|
| Receptor-mediated tobacco toxicity: acceleration of sequential expression of alpha5 and alpha7 nicotinic receptor subunits in oral keratinocytes exposed to cigarette smoke. | 2008 May |
|
| Enhanced nicotine sensitivity in nociceptin/orphanin FQ receptor knockout mice. | 2009 Apr |
|
| Distinct effects of nociceptin analogs on scopolamine-induced memory impairment in mice. | 2009 Jan 14 |
|
| Effects of mecamylamine on nicotine-induced conditioned hyperactivity and sensitization in differentially reared rats. | 2009 Jul |
|
| Nicotine anxiogenic and rewarding effects are decreased in mice lacking beta-endorphin. | 2009 Jun |
|
| Corticotropin-releasing factor within the central nucleus of the amygdala and the nucleus accumbens shell mediates the negative affective state of nicotine withdrawal in rats. | 2009 Jun |
|
| Cardiovascular effect of peripheral injected melittin in normotensive conscious rats: Mediation of the central cholinergic system. | 2009 Nov-Dec |
|
| The limbic circuitry underlying cocaine seeking encompasses the PPTg/LDT. | 2009 Oct |
|
| Repetitive nicotine exposure leads to a more malignant and metastasis-prone phenotype of SCLC: a molecular insight into the importance of quitting smoking during treatment. | 2010 Aug |
|
| Nicotinic receptor-mediated reduction in L-DOPA-induced dyskinesias may occur via desensitization. | 2010 Jun |
|
| Neuronal nicotinic acetylcholine receptors as pharmacotherapeutic targets for the treatment of alcohol use disorders. | 2010 Mar |
|
| Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes. | 2010 May |
|
| Ryanodine receptor-2 upregulation and nicotine-mediated plasticity. | 2011 Jan 5 |
Patents
Sample Use Guides
Usual Adult Dose for Hypertension
2.5 mg orally twice a day; may increase by one 2.5 mg tablet at intervals of 2 days or more until desired blood pressure response is achieved.
Comments:
-The average total daily dose is 25 mg, usually in 3 divided doses; however, 2.5 mg daily may be sufficient. Partial tolerance may develop in certain patients, which requires an increase in the total daily dose.
-Four or more doses may be required when smooth control is difficult to obtain.
-Titration should be determined by blood pressure readings in the erect position at the time of maximal effect of this drug, as well as by signs and symptoms of orthostatic hypotension. In severe or urgent cases, titration at larger increments and shorter intervals may be needed.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment:: Racemic mecamylamine and its stereoisomers
were tested for their ability to inhibit the ACh-evoked
responses of a4b2, a3b4, a3b2, and a7 type receptors expressed
in Xenopus oocytes.
10 uM of either mecamylamine stereoisomer produced significant inhibition
of the nAChR subtypes.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 11:03:34 UTC 2021
by
admin
on
Sat Jun 26 11:03:34 UTC 2021
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| Record UNII |
6EE945D3OK
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| Record Status |
Validated (UNII)
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| Record Version |
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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WHO-ATC |
C02BB01
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NCI_THESAURUS |
C66886
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NDF-RT |
N0000175641
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FDA ORPHAN DRUG |
117598
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EPA PESTICIDE CODE |
600090
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LIVERTOX |
585
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NDF-RT |
N0000175644
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WHO-VATC |
QC02BB01
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542
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6147-18-8
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PRIMARY | |||
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60-40-2
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NON-SPECIFIC STEREOCHEMISTRY | |||
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DB00657
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PRIMARY | |||
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6EE945D3OK
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PRIMARY | |||
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6673
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PRIMARY | RxNorm | ||
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SUB08670MIG
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3990
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MECAMYLAMINE
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1646
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PRIMARY | |||
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60-40-2
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PRIMARY | |||
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C66063
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PRIMARY | |||
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D008464
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PRIMARY | |||
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M7113
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PRIMARY | Merck Index | ||
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200-476-1
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PRIMARY | |||
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CHEMBL267936
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ACTIVE MOIETY |
