Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB01556
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
Identification
- Generic Name
- Chlorphentermine
- DrugBank Accession Number
- DB01556
- Background
A sympathomimetic agent that was formerly used as an anorectic. It has properties similar to those of dextroamphetamine. It has been implicated in lipid storage disorders and pulmonary hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1223)
- Type
- Small Molecule
- Groups
- Illicit, Withdrawn
- Structure
Structure for Chlorphentermine (DB01556)
- Weight
- Average: 183.678
Monoisotopic: 183.08147716 - Chemical Formula
- C10H14ClN
- Synonyms
- 4-Chloro-a,a-dimethylbenzeneethanamine
- 4-Chloro-a,a-dimethylphenethylamine
- a,a-Dimethyl-p-chlorophenethylamine
- Chlorphentermine
- Chlorphenterminum
- Clorfentermina
Pharmacology
- Indication
Used as an appetite suppressant.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Chlorphentermine is a relatively weak stimulant with little abuse potential. It presents a prominent serotonergic profile leading to pulmonary hypertension and cardiac fibrosis after prolonged use. Thus, this drug is no longer used.
- Mechanism of action
Target Actions Organism ASodium-dependent serotonin transporter modulatorHumans - Absorption
Well absorbed following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
40 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Acebutolol can be decreased when used in combination with Chlorphentermine. Aceclofenac The risk or severity of hypertension can be increased when Chlorphentermine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Chlorphentermine is combined with Acemetacin. Acetazolamide Acetazolamide may decrease the excretion rate of Chlorphentermine which could result in a higher serum level. Acetophenazine Acetophenazine may decrease the stimulatory activities of Chlorphentermine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Chlorphentermine hydrochloride RL11HOJ7DM 151-06-4 WEJDYJKJPUPMLH-UHFFFAOYSA-N - International/Other Brands
- Apsedon / Desopimon / Lucofen
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenethylamines
- Direct Parent
- Amphetamines and derivatives
- Alternative Parents
- Phenylpropanes / Chlorobenzenes / Aralkylamines / Aryl chlorides / Organopnictogen compounds / Organochlorides / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Halobenzene / Hydrocarbon derivative / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- amphetamines (CHEBI:3646)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- NHW07912O7
- CAS number
- 461-78-9
- InChI Key
- ZCKAMNXUHHNZLN-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3
- IUPAC Name
- 1-(4-chlorophenyl)-2-methylpropan-2-amine
- SMILES
- CC(C)(N)CC1=CC=C(Cl)C=C1
References
- General References
- GYLYS JA, HART JJ, WARREN MR: Chlorphentermine, a new anorectic agent. J Pharmacol Exp Ther. 1962 Sep;137:365-73. [Article]
- External Links
- KEGG Compound
- C07559
- PubChem Compound
- 10007
- PubChem Substance
- 46505599
- ChemSpider
- 9613
- BindingDB
- 85704
- ChEBI
- 3646
- ChEMBL
- CHEMBL1201269
- ZINC
- ZINC000000122765
- Wikipedia
- Chlorphentermine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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 boiling point (°C) 100-102 °C at 2.00E+00 mm Hg Not Available logP 2.60 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.105 mg/mL ALOGPS logP 2.81 ALOGPS logP 2.69 Chemaxon logS -3.2 ALOGPS pKa (Strongest Basic) 10.24 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 26.02 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 53.15 m3·mol-1 Chemaxon Polarizability 20.19 Å3 Chemaxon Number of Rings 1 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 + 0.9966 Blood Brain Barrier + 0.9792 Caco-2 permeable + 0.7531 P-glycoprotein substrate Non-substrate 0.6627 P-glycoprotein inhibitor I Non-inhibitor 0.9092 P-glycoprotein inhibitor II Non-inhibitor 0.9805 Renal organic cation transporter Non-inhibitor 0.8185 CYP450 2C9 substrate Non-substrate 0.8464 CYP450 2D6 substrate Substrate 0.5148 CYP450 3A4 substrate Non-substrate 0.5233 CYP450 1A2 substrate Inhibitor 0.6449 CYP450 2C9 inhibitor Non-inhibitor 0.8526 CYP450 2D6 inhibitor Inhibitor 0.8286 CYP450 2C19 inhibitor Non-inhibitor 0.752 CYP450 3A4 inhibitor Non-inhibitor 0.5737 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7748 Ames test Non AMES toxic 0.8728 Carcinogenicity Non-carcinogens 0.6055 Biodegradation Not ready biodegradable 0.9895 Rat acute toxicity 2.8974 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9818 hERG inhibition (predictor II) Non-inhibitor 0.738
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4i-9500000000-688c22dbc0d433451811 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-016r-0900000000-711b624e72e64785f050 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0159-0900000000-8de2111fa7decdb61ada Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0900000000-00df956db6d77fbc1f1e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00lr-0900000000-d6cc6c79768922bbd75f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-5900000000-23866fefa15f11529bba Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056s-5900000000-f7f2b48f863eae870196 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 139.3568 predictedDeepCCS 1.0 (2019) [M+H]+ 142.72458 predictedDeepCCS 1.0 (2019) [M+Na]+ 152.09135 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
- Specific Function
- actin filament binding
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at July 31, 2007 13:10 / Updated at November 05, 2024 05:28