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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyFludiazepam
Identification
- Name
- Fludiazepam
- Accession Number
- DB01567
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Description
Fludiazepam is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is a scheduled drug in the U.S., but is approved for use in Japan.
- Structure
Structure for Fludiazepam (DB01567)
- Synonyms
- 7-chloro-5-(O-Fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one
- Erispan
- Fludiazepamum
- International/Other Brands
- Erispan (Sumitomo)
- Categories
- Anti-Anxiety Agents
- Benzazepines
- Benzodiazepines and benzodiazepine derivatives
- Benzodiazepinones
- Central Nervous System Agents
- Central Nervous System Depressants
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Nervous System
- Peripheral Nervous System Agents
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- UNII
- 7F64A2K16Z
- CAS number
- 3900-31-0
- Weight
- Average: 302.731
Monoisotopic: 302.062218928 - Chemical Formula
- C16H12ClFN2O
- InChI Key
- ROYOYTLGDLIGBX-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
- IUPAC Name
- 7-chloro-5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
- SMILES
- CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F
Pharmacology
- Indication
Used for the short-term treatment of anxiety disorders.
- Pharmacodynamics
Fludiazepam is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Fludiazepam accumulates primarily in the cortex and thalamus.
- Mechanism of action
Fludiazepam has similar action to diazepam, but binds with four times more affinity to benzodiazepine receptors than diazepam.
- Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hepatic.
- Route of elimination
- Not Available
- Half life
- Not Available
- Clearance
- Not Available
- Toxicity
Symptoms of overdose include drowsiness, weakness, nausea, dizziness, abdominal pain, cerebral oedema and renal tubular necrosis, hyperglycaemia and hypoglycaemia, liver damage, encephalopathy, coma and death.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 3-isobutyl-1-methyl-7H-xanthine The therapeutic efficacy of Fludiazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine. 3,4-Methylenedioxyamphetamine The risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Fludiazepam. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Fludiazepam. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Fludiazepam. 6-O-benzylguanine The therapeutic efficacy of Fludiazepam can be decreased when used in combination with 6-O-benzylguanine. 7-Deazaguanine The therapeutic efficacy of Fludiazepam can be decreased when used in combination with 7-Deazaguanine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Fludiazepam is combined with 7-Nitroindazole. 7,9-Dimethylguanine The therapeutic efficacy of Fludiazepam can be decreased when used in combination with 7,9-Dimethylguanine. 8-azaguanine The therapeutic efficacy of Fludiazepam can be decreased when used in combination with 8-azaguanine. 8-chlorotheophylline The therapeutic efficacy of Fludiazepam can be decreased when used in combination with 8-chlorotheophylline. - Food Interactions
- Avoid alcohol.
- Avoid excessive quantities of coffee or tea (Caffeine).
- Avoid taking with grapefruit juice.
References
- Synthesis Reference
Yamamato, H., Inaba, S.,Okamoto, T., Hirohashi, T., Ishizumi, K., Yamamoto, M., Maruyama, l., Mori, K. and Kobayashi, T.; U.S. Patents 3,723,461; March 27, 1973; 3,828,027; August 6, 1974 and 3,925,364; December 9, 1975; all assigned to Sumitomo Chemical Co., Ltd.
- General References
- Ishiwata K, Yanai K, Ido T, Miura-Kanno Y, Kawashima K: Synthesis and biodistribution of [11C]fludiazepam for imaging benzodiazepine receptors. Int J Rad Appl Instrum B. 1988;15(4):365-71. [PubMed:2855634]
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- External Links
- Human Metabolome Database
- HMDB0015513
- KEGG Drug
- D01354
- PubChem Compound
- 3369
- PubChem Substance
- 46507563
- ChemSpider
- 3252
- ChEBI
- 31618
- ChEMBL
- CHEMBL13291
- Therapeutic Targets Database
- DAP000934
- PharmGKB
- PA164745609
- Wikipedia
- Fludiazepam
- ATC Codes
- N05BA17 — Fludiazepam
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 218.5-219 Yamamato, H., Inaba, S.,Okamoto, T., Hirohashi, T., Ishizumi, K., Yamamoto, M., Maruyama, l., Mori, K. and Kobayashi, T.; U.S. Patents 3,723,461; March 27, 1973; 3,828,027; August 6, 1974 and 3,925,364; December 9, 1975; all assigned to Sumitomo Chemical Co., Ltd. logP 2.75 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0144 mg/mL ALOGPS logP 2.83 ALOGPS logP 3.22 ChemAxon logS -4.3 ALOGPS pKa (Strongest Basic) 1.89 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 32.67 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 80.03 m3·mol-1 ChemAxon Polarizability 29.45 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9946 Caco-2 permeable + 0.8567 P-glycoprotein substrate Substrate 0.6618 P-glycoprotein inhibitor I Inhibitor 0.5293 P-glycoprotein inhibitor II Non-inhibitor 0.8532 Renal organic cation transporter Inhibitor 0.592 CYP450 2C9 substrate Non-substrate 0.6724 CYP450 2D6 substrate Non-substrate 0.9087 CYP450 3A4 substrate Substrate 0.8081 CYP450 1A2 substrate Inhibitor 0.7925 CYP450 2C9 inhibitor Non-inhibitor 0.5446 CYP450 2D6 inhibitor Non-inhibitor 0.8884 CYP450 2C19 inhibitor Inhibitor 0.5598 CYP450 3A4 inhibitor Inhibitor 0.5153 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5827 Ames test Non AMES toxic 0.8792 Carcinogenicity Non-carcinogens 0.817 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.2719 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9953 hERG inhibition (predictor II) Non-inhibitor 0.8236
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0uk9-2794000000-6f1a3e2e0783b2069f2f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodiazepines
- Sub Class
- 1,4-benzodiazepines
- Direct Parent
- 1,4-benzodiazepines
- Alternative Parents
- Alpha amino acids and derivatives / Fluorobenzenes / Aryl fluorides / Aryl chlorides / Tertiary carboxylic acid amides / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds show 5 more
- Substituents
- 1,4-benzodiazepine / Alpha-amino acid or derivatives / Fluorobenzene / Halobenzene / Aryl chloride / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, organochlorine compound, 1,4-benzodiazepinone (CHEBI:31618)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA2
- Uniprot ID
- P47869
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-2
- Molecular Weight
- 51325.85 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA3
- Uniprot ID
- P34903
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-3
- Molecular Weight
- 55164.055 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Transporter activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA5
- Uniprot ID
- P31644
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-5
- Molecular Weight
- 52145.645 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRG1
- Uniprot ID
- Q8N1C3
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-1
- Molecular Weight
- 53594.49 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRG2
- Uniprot ID
- P18507
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-2
- Molecular Weight
- 54161.78 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRG3
- Uniprot ID
- Q99928
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-3
- Molecular Weight
- 54288.16 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRB1
- Uniprot ID
- P18505
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-1
- Molecular Weight
- 54234.085 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRB2
- Uniprot ID
- P47870
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-2
- Molecular Weight
- 59149.895 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-gated chloride ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRB3
- Uniprot ID
- P28472
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-3
- Molecular Weight
- 54115.04 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRD
- Uniprot ID
- O14764
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit delta
- Molecular Weight
- 50707.835 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRE
- Uniprot ID
- P78334
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit epsilon
- Molecular Weight
- 57971.175 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the ute...
- Gene Name
- GABRP
- Uniprot ID
- O00591
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit pi
- Molecular Weight
- 50639.735 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA...
- Gene Name
- GABRR1
- Uniprot ID
- P24046
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit rho-1
- Molecular Weight
- 55882.91 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA...
- Gene Name
- GABRR2
- Uniprot ID
- P28476
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit rho-2
- Molecular Weight
- 54150.41 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRR3
- Uniprot ID
- A8MPY1
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit rho-3
- Molecular Weight
- 54271.1 Da
References
- Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046]
Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:03