Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H29NO2 |
Molecular Weight | 339.4712 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=O)O[C@@](CC1=CC=CC=C1)([C@H](C)CN(C)C)C2=CC=CC=C2
InChI
InChIKey=XLMALTXPSGQGBX-GCJKJVERSA-N
InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6151117 | https://www.ncbi.nlm.nih.gov/pubmed/21215785 | https://www.drugs.com/propoxyphene.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6151117 | https://www.ncbi.nlm.nih.gov/pubmed/21215785 | https://www.drugs.com/propoxyphene.html
Propoxyphene is a centrally acting opiate analgesic. Propoxyphene is an odorless, freely soluble in water, white crystalline powder with a bitter taste. In vitro studies demonstrated propoxyphene and the metabolite norpropoxyphene inhibit sodium channels (local anesthetic effect) with norpropoxyphene being approximately 2 fold more potent than propoxyphene and propoxyphene approximately 10 fold more potent than lidocaine. Propoxyphene and norpropoxyphene inhibit the voltage-gated potassium current carried by cardiac rapidly activating delayed rectifier (hERG) channels with approximately equal potency. It is unclear if the effects on ion channels occur within therapeutic dose range. Propoxyphene is indicated for the relief of mild to moderate pain.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6151117 |
53.0 nM [Kd] | ||
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6151117 |
140.0 nM [Kd] | ||
Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6151117 |
2100.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DARVON COMPOUND-65 Approved UseThis product is indicated for the relief of mild to moderate pain, either when pain is present alone or when it is accompanied by fever. Launch Date-3.83011193E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2310 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7391940/ |
7.5 mg/kg single, oral dose: 7.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
NORPROPOXYPHENE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
459 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7391940/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NORPROPOXYPHENE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
126000 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7391940/ |
7.5 mg/kg single, oral dose: 7.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
NORPROPOXYPHENE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2440 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7391940/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NORPROPOXYPHENE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7391940/ |
7.5 mg/kg single, oral dose: 7.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
NORPROPOXYPHENE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7391940/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NORPROPOXYPHENE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1700 mg 1 times / day multiple, oral Highest studied dose Dose: 1700 mg, 1 times / day Route: oral Route: multiple Dose: 1700 mg, 1 times / day Sources: |
unhealthy, 29 years n = 1 Health Status: unhealthy Condition: heroin dependence Age Group: 29 years Sex: M Population Size: 1 Sources: |
Other AEs: Seizure... |
1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Disc. AE: Emesis, Blurred vision... Other AEs: Feeling detached, Dizziness... AEs leading to discontinuation/dose reduction: Emesis (3.1%) Other AEs:Blurred vision (3.1%) Feeling detached (12.5%) Sources: Dizziness (3.1%) Drowsiness (6.2%) Nervous (6.2%) Shaking (6.2%) Headaches (6.2%) Hangover (3.1%) Taste metallic (6.2%) Cramps leg (3.1%) Upset stomach (6.2%) Constipation (6.2%) |
200 mg 1 times / day single, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: single Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult n = 48 Health Status: unhealthy Condition: pain Age Group: adult Sex: M+F Population Size: 48 Sources: |
Other AEs: Dizziness, Diaphoresis... Other AEs: Dizziness (grade 3, 4.2%) Sources: Diaphoresis (grade 3, 2.1%) |
800 mg 1 times / day multiple, oral (mean) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, adult n = 272 Health Status: unhealthy Condition: heroin dependence Age Group: adult Sex: M+F Population Size: 272 Sources: |
Other AEs: Dysphoria... |
800 mg 1 times / day multiple, oral (starting) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, mean age 28.5 years n = 32 Health Status: unhealthy Condition: heroin dependence Age Group: mean age 28.5 years Sex: M+F Population Size: 32 Sources: |
Other AEs: Constipation, Delirium... Other AEs: Constipation Sources: Delirium Dysphoria Euphoria Sedation |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Seizure | 1700 mg 1 times / day multiple, oral Highest studied dose Dose: 1700 mg, 1 times / day Route: oral Route: multiple Dose: 1700 mg, 1 times / day Sources: |
unhealthy, 29 years n = 1 Health Status: unhealthy Condition: heroin dependence Age Group: 29 years Sex: M Population Size: 1 Sources: |
|
Feeling detached | 12.5% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Cramps leg | 3.1% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Dizziness | 3.1% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Hangover | 3.1% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Blurred vision | 3.1% Disc. AE |
1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Emesis | 3.1% Disc. AE |
1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Constipation | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Drowsiness | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Headaches | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Nervous | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Shaking | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Taste metallic | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Upset stomach | 6.2% | 1000 mg 1 times / day multiple, oral (mean) Studied dose Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: heroin and methadone dependence Age Group: adult Sex: M+F Population Size: 32 Sources: |
Diaphoresis | grade 3, 2.1% | 200 mg 1 times / day single, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: single Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult n = 48 Health Status: unhealthy Condition: pain Age Group: adult Sex: M+F Population Size: 48 Sources: |
Dizziness | grade 3, 4.2% | 200 mg 1 times / day single, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: single Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult n = 48 Health Status: unhealthy Condition: pain Age Group: adult Sex: M+F Population Size: 48 Sources: |
Dysphoria | grade 1 | 800 mg 1 times / day multiple, oral (mean) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, adult n = 272 Health Status: unhealthy Condition: heroin dependence Age Group: adult Sex: M+F Population Size: 272 Sources: |
Constipation | 800 mg 1 times / day multiple, oral (starting) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, mean age 28.5 years n = 32 Health Status: unhealthy Condition: heroin dependence Age Group: mean age 28.5 years Sex: M+F Population Size: 32 Sources: |
|
Delirium | 800 mg 1 times / day multiple, oral (starting) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, mean age 28.5 years n = 32 Health Status: unhealthy Condition: heroin dependence Age Group: mean age 28.5 years Sex: M+F Population Size: 32 Sources: |
|
Dysphoria | 800 mg 1 times / day multiple, oral (starting) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, mean age 28.5 years n = 32 Health Status: unhealthy Condition: heroin dependence Age Group: mean age 28.5 years Sex: M+F Population Size: 32 Sources: |
|
Euphoria | 800 mg 1 times / day multiple, oral (starting) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, mean age 28.5 years n = 32 Health Status: unhealthy Condition: heroin dependence Age Group: mean age 28.5 years Sex: M+F Population Size: 32 Sources: |
|
Sedation | 800 mg 1 times / day multiple, oral (starting) Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy, mean age 28.5 years n = 32 Health Status: unhealthy Condition: heroin dependence Age Group: mean age 28.5 years Sex: M+F Population Size: 32 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major [Ki 3.5 uM] | ||||
yes [IC50 63.3 uM] | ||||
yes | ||||
yes | yes (co-administration study) Comment: Propoxyphene inhibits CYP2D6-mediated hepatic clearance of metoprolol |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/10690289/ |
||||
Sources: https://pubmed.ncbi.nlm.nih.gov/10690289/ |
||||
PubMed
Title | Date | PubMed |
---|---|---|
Potentially inappropriate prescribing in Canada relative to the US. | 2004 |
|
30-MINUTES-TUMT. Use of the visual analogue scale to investigate patients' pain perception, different cocktail options and tolerability during 30 minutes' treatment. | 2004 |
|
Titanium pigment in tissues of drug addicts: report of 5 necropsied cases. | 2004 Apr |
|
Self-reported drug use and urinalysis results. | 2004 Jan |
|
Propoxyphene use in the elderly. | 2004 Jul |
|
[Plasma assay of methadone enantiomers with high performance liquid chromatography]. | 2004 May |
|
Improvement of pain treatment after major abdominal surgery by intravenous S+-ketamine. | 2004 May |
|
CYP3A4 mediates dextropropoxyphene N-demethylation to nordextropropoxyphene: human in vitro and in vivo studies and lack of CYP2D6 involvement. | 2004 Oct |
|
Investigating the environmental transport of human pharmaceuticals to streams in the United Kingdom. | 2004 Oct 15 |
|
Evaluation of the Triage PPY on-site testing device for the detection of dextropropoxyphene in urine. | 2004 Sep |
|
Urine concentrations of fentanyl and norfentanyl during application of Duragesic transdermal patches. | 2004 Sep |
|
Criteria for prescribing require further study. | 2004 Sep |
|
Inappropriately defining "inappropriate medication for the elderly". | 2004 Sep |
|
The occurrence of selected human pharmaceutical compounds in UK estuaries. | 2004 Sep |
|
Intermittent injection of bupivacaine into the margin or the cavity after reduction mammaplasty. | 2005 |
|
Prevalence of opioid adverse events in chronic non-malignant pain: systematic review of randomised trials of oral opioids. | 2005 |
|
ECG abnormalities in co-proxamol (paracetamol/dextropropoxyphene) poisoning. | 2005 |
|
Dextropropoxyphene: safety and efficacy in older patients. | 2005 |
|
Simultaneous determination of paracetamol and dextropropoxyphene in human plasma by liquid chromatography/tandem mass spectrometry: application to clinical bioequivalence studies. | 2005 |
|
Relation of postmortem blood alcohol and drug concentrations in fatal poisonings involving amitriptyline, propoxyphene and promazine. | 2005 Aug |
|
Paracetamol + dextropropoxyphene: planned withdrawal from the British market. | 2005 Aug |
|
Usage of paracetamol-containing combination analgesics remains high in primary care. | 2005 Dec |
|
A multicentre study of coproxamol poisoning suicides based on coroners' records in England. | 2005 Feb |
|
'Opioid poisoning deaths in New Zealand (2001-2002)' and the UK's recent decision to withdraw the pain killer coproxamol. | 2005 Feb 11 |
|
Opioid poisoning deaths in New Zealand (2001-2002). | 2005 Feb 11 |
|
The role of tramadol in cancer pain treatment--a review. | 2005 Jan |
|
The impact of P-glycoprotein on the disposition of drugs targeted for indications of the central nervous system: evaluation using the MDR1A/1B knockout mouse model. | 2005 Jan |
|
In the days of patients' choice, why is the patient being ignored? | 2005 Jul 23-29 |
|
Acute pain management pharmacology for the patient with concurrent renal or hepatic disease. | 2005 Jun |
|
A randomized, double-blind, placebo controlled triphosphate in study of oral adenosine subacute low back pain. | 2005 Jun |
|
Co-proxamol and suicide: preventing the continuing toll of overdose deaths. | 2005 Mar |
|
Impact of paracetamol pack size restrictions on poisoning from paracetamol in England and Wales: an observational study. | 2005 Mar |
|
Are incorrectly used drugs more frequently involved in adverse drug reactions? A prospective study. | 2005 May |
|
Clinical toxicology: clinical science to public health. | 2005 Nov |
|
Bupivacaine/ketamine is superior to intra-articular ketamine analgesia following arthroscopic knee surgery. | 2005 Oct |
|
[Over-the-counter paracetamol a common cause of poisoning among teenage girls. The Poison Control Center's report on analgesics poisoning]. | 2005 Oct 24-30 |
|
National trends in and predictors of propoxyphene use in community-dwelling older adults. | 2005 Sep |
|
Pain and pain treatments in European palliative care units. A cross sectional survey from the European Association for Palliative Care Research Network. | 2005 Sep |
|
Drug therapy in dental practice: nonopioid and opioid analgesics. | 2005 Winter |
|
Time-trends in method-specific suicide rates compared with the availability of specific compounds. The Danish experience. | 2006 |
|
Dextropropoxyphene combinations: Swedish market withdrawal. | 2006 Feb |
|
Analgesic effect of electroacupuncture in postthoracotomy pain: a prospective randomized trial. | 2006 Jun |
|
Consumer group urges Food and Drug Administration to ban drug Darvon. | 2006 Jun |
|
Development of opioid formulations with limited diversion and abuse potential. | 2006 Jun |
|
[Patterns of prescription and usage of triptans in Alsace (France): misuse is frequent and avoidable]. | 2006 Mar |
|
Profound metoprolol-induced bradycardia precipitated by acetaminophen-propoxyphene. | 2006 Mar |
|
Differential in vitro inhibition of M3G and M6G formation from morphine by (R)- and (S)-methadone and structurally related opioids. | 2006 Mar |
|
The occurrence of selected pharmaceuticals in wastewater effluent and surface waters of the lower Tyne catchment. | 2006 Mar 1 |
|
Propoxyphene-induced hypoglycemia in renal failure. | 2006 Mar-Apr |
|
Survival after marked hyperlactaemia. | 2006 May |
Sample Use Guides
Darvon-N (Propoxyphene) is given orally. The usual dosage is one 100 mg propoxyphene napsylate tablet every 4 hours as needed for pain. The maximum dose of Darvon-N is 6 tablets per day. Do not exceed the maximum daily dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21215785
Cell membrane preparation (Chemiscreen™ MOR) expressing recombinant human MOR were used for activity evaluation. The assays were performed in microtiter plates with 40 mkL of binding buffer or Propoxyphene (1–100,000 mkM), 10 mkL of radioligand (2 nM (3H)-DAMG), and 50 mkL of diluted membranes with three wells per group. The plates were then incubated at room temperature for 2h. The binding incubation was terminated by the addition of 100 mkL cold binding buffer to each well. The glass fiber filter plates were presoaked for 30–45 min with 0.33% PEI buffer. The PEI solution was removed from the filter plate with a vacuum manifold (Millipore) and the filters washed with 200 mkL priming buffer (50 mM HEPES, 0.5% BSA, pH 7.4) per well. The binding reaction was transferred to the filter plate and washed with 200 mkL washing buffer (50 mM HEPES with 500 mM NaCl and 0.1% BSA, pH 7.4).
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67413
Created by
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NCI_THESAURUS |
C241
Created by
admin on Fri Dec 15 14:59:35 UTC 2023 , Edited by admin on Fri Dec 15 14:59:35 UTC 2023
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Code System | Code | Type | Description | ||
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2621-61-6
Created by
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II2G62OV6F
Created by
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C61711
Created by
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PRIMARY | |||
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10100
Created by
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PRIMARY | |||
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100000078898
Created by
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PRIMARY | |||
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77-50-9
Created by
admin on Fri Dec 15 14:59:35 UTC 2023 , Edited by admin on Fri Dec 15 14:59:35 UTC 2023
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NON-SPECIFIC STEREOCHEMISTRY |
ACTIVE MOIETY