chlorphenamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
616 132-22-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • chlorphenamine
  • chloropheniramine
  • chlorophenylpyridamine
  • chloroprophenpyridamine
  • chlorpheniramine
  • chlorprophenpyridamine
  • chlorpheniramine maleate
  • chlorpheniramine tannate
  • chlorpheniramine polistirex
A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.
  • Molecular weight: 274.79
  • Formula: C16H19ClN2
  • CLOGP: 3.15
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 16.13
  • ALOGS: -3.72
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
12 mg O
12 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.48 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 41 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.70 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 22 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 15, 1950 FDA BAYER HEALTHCARE LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dilatation intrahepatic duct acquired 247.09 44.72 29 399 59 2357598
Toxicity to various agents 180.75 44.72 55 373 32699 2324958
Overdose 146.83 44.72 42 386 19865 2337792
Death 145.57 44.72 59 369 81409 2276248
Hepatotoxicity 140.51 44.72 29 399 3452 2354205
Venoocclusive liver disease 109.76 44.72 18 410 590 2357067
Drug abuse 100.14 44.72 28 400 11998 2345659
Vomiting 91.00 44.72 41 387 71561 2286096
Liver function test abnormal 83.59 44.72 22 406 7468 2350189
Venoocclusive disease 78.05 44.72 12 416 256 2357401
Cardiac arrest 76.94 44.72 24 404 14906 2342751
Intentional overdose 70.21 44.72 21 407 11300 2346357
Depressed level of consciousness 69.08 44.72 19 409 7585 2350072
Completed suicide 68.86 44.72 24 404 21010 2336647
Tonsillar hypertrophy 57.98 44.72 9 419 204 2357453
Agitation 53.62 44.72 17 411 11034 2346623
Subdural haemorrhage 50.08 44.72 9 419 504 2357153
Seizure 47.28 44.72 19 409 24447 2333210

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 244.98 61.23 63 330 13626 1732762
Toxicity to various agents 219.17 61.23 68 325 29073 1717315
Overdose 91.39 61.23 31 362 16670 1729718
Respiratory arrest 84.64 61.23 23 370 5816 1740572
Completed suicide 80.30 61.23 28 365 16284 1730104
Cardiac arrest 77.06 61.23 27 366 15903 1730485
Intentional product misuse 66.19 61.23 20 373 7338 1739050
Death 64.63 61.23 40 353 87403 1658985
Tachycardia 63.24 61.23 22 371 12606 1733782

Pharmacologic Action:

SourceCodeDescription
ATC R06AB04 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Substituted alkylamines
ATC R06AB54 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Substituted alkylamines
CHEBI has role CHEBI:50949 serotonin uptake inhibitor
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:37956 histamine antagonist
CHEBI has role CHEBI:59683 antipruritic drug
CHEBI has role CHEBI:50857 anti-allergic agent
MeSH PA D018926 Anti-Allergic Agents
MeSH PA D000982 Antipruritics
MeSH PA D003879 Dermatologic Agents
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D018377 Neurotransmitter Agents
FDA MoA N0000000190 Histamine H1 Receptor Antagonists
FDA EPC N0000175587 Histamine-1 Receptor Antagonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Dermatographic urticaria indication 7632005 DOID:743
Vasomotor rhinitis indication 8229003 DOID:4730
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Sneezing indication 76067001
Common cold indication 82272006 DOID:10459
Urticaria indication 126485001
Influenza-like symptoms indication 315642008
Seasonal allergic rhinitis indication 367498001
Itching of skin indication 418363000
Allergic conjunctivitis indication 473460002 DOID:11204
Brain damage contraindication 2470005
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Goiter contraindication 3716002 DOID:12176
Ocular hypertension contraindication 4210003 DOID:9282
Gastritis contraindication 4556007 DOID:4029
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Asthenia contraindication 13791008
Hyperkalemia contraindication 14140009
Severe chronic ulcerative colitis contraindication 14311001
Constipation contraindication 14760008 DOID:2089
Disorder of autonomic nervous system contraindication 15241006
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Hashimoto thyroiditis contraindication 21983002
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Ventricular tachycardia contraindication 25569003
Acute tuberculosis contraindication 25629007
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hypercapnia contraindication 29596007
Bronchitis contraindication 32398004 DOID:6132
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Hypovolemic shock contraindication 39419009
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Body fluid retention contraindication 43498006
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Acidosis contraindication 51387008
Gastrointestinal perforation contraindication 51875005
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Paralytic ileus contraindication 55525008 DOID:8442
Peptic reflux disease contraindication 57643001
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Blood coagulation disorder contraindication 64779008 DOID:1247
Arterial thrombosis contraindication 65198009
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Psychotic disorder contraindication 69322001
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Arteriosclerotic vascular disease contraindication 72092001
Diabetes mellitus contraindication 73211009 DOID:9351
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Urethral stricture contraindication 76618002
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Cor pulmonale contraindication 83291003 DOID:8515
Hiatal hernia contraindication 84089009 DOID:12642
Epilepsy contraindication 84757009 DOID:1826
Pulmonary emphysema contraindication 87433001
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Hemophilia contraindication 90935002
Myasthenia gravis contraindication 91637004 DOID:437
Dermatitis herpetiformis contraindication 111196000 DOID:8505
Anemia due to enzyme deficiency contraindication 111577008
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
Gastrointestinal obstruction contraindication 126765001
Neoplasm of brain contraindication 126952004 DOID:1319
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Drug-induced psychosis contraindication 191483003 DOID:1742
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Partial atrioventricular block contraindication 195039008
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Coronary artery bypass graft contraindication 232717009
Myocardial dysfunction contraindication 233928007
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Morbid obesity contraindication 238136002 DOID:11981
Hypocomplementemic urticarial vasculitis contraindication 239945009
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Drowsy contraindication 271782001
Exacerbation of asthma contraindication 281239006
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Panic disorder contraindication 371631005 DOID:594
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Cardiovascular event risk contraindication 395112001
Pseudomembranous enterocolitis contraindication 397683000
Gastric ulcer contraindication 397825006 DOID:10808
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Central nervous system depression contraindication 418072004
Ultrarapid metabolizer due to cytochrome p450 CYP2D6 variant contraindication 422681000
Fever greater than 100.4 Fahrenheit contraindication 426000000
Dysfunction of sphincter of Oddi contraindication 430887001
Hypertensive urgency contraindication 443482000
Acute erosive gastritis contraindication 444926003
Smokes tobacco daily contraindication 449868002
Acute exacerbation of asthma contraindication 708038006
Acute Thromboembolic Stroke contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.47 Basic
pKa2 4.14 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
8MG TUXARIN ER MAINPOINTE N206323 June 22, 2015 RX TABLET, EXTENDED RELEASE ORAL 9066942 Jan. 3, 2032 TREATMENT OF COUGH AND SYMPTOMS ASSOCIATED WITH UPPER RESPIRATORY ALLERGIES OR A COMMON COLD WITH CODEINE PHOSPHATE AND CHLORPHENIRAMINE MALEATE ORALLY ADMINISTERED EXTENDED RELEASE TABLETS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Histamine H1 receptor GPCR ANTAGONIST Ki 8.15 WOMBAT-PK CHEMBL
Sodium-dependent noradrenaline transporter Transporter Kd 5.84 SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 2B GPCR Ki 5.17 PDSP
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.96 CHEMBL
Lethal(3)malignant brain tumor-like protein 3 Unclassified IC50 4.38 CHEMBL
Lethal(3)malignant brain tumor-like protein 1 Unclassified IC50 4.39 CHEMBL
MBT domain-containing protein 1 Unclassified IC50 4.47 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5 CHEMBL
Histamine H4 receptor GPCR Ki 6.67 WOMBAT-PK
Cytochrome P450 2D6 Enzyme Ki 4.97 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Kd 5.97 SCIENTIFIC LITERATURE
Sodium-dependent serotonin transporter Transporter Kd 7.82 WOMBAT-PK
Chloroquine resistance transporter Unclassified IC50 4.27 CHEMBL
Histamine H1 receptor GPCR IC50 8.06 CHEMBL
Histamine H1 receptor GPCR Ki 8.70 CHEMBL

External reference:

IDSource
D002744 MESH_DESCRIPTOR_UI
4017865 VUID
N0000146218 NUI
C0008281 UMLSCUI
D00665 KEGG_DRUG
3U6IO1965U UNII
104 INN_ID
1405-56-7 SECONDARY_CAS_RN
372914003 SNOMEDCT_US
9944001 SNOMEDCT_US
4017865 VANDF
93262 MMSL
004430 NDDF
3966 MMSL
2400 RXNORM
d00191 MMSL
32347 MMSL
CHEBI:52010 CHEBI
CHEMBL505 ChEMBL_ID
DB01114 DRUGBANK_ID
CHEMBL1659 ChEMBL_ID
6976 IUPHAR_LIGAND_ID
2725 PUBCHEM_CID
CHEMBL1201659 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
CHILDRENS DIMETAPP LONG ACTING COUGH PLUS COLD HUMAN OTC DRUG LABEL 2 0031-2238 SOLUTION 2 mg ORAL OTC MONOGRAPH FINAL 9 sections
Childrens Robitussin Nighttime Cough Long-Acting DM HUMAN OTC DRUG LABEL 2 0031-8692 SOLUTION 2 mg ORAL OTC MONOGRAPH FINAL 9 sections
CHILDRENS ROBITUSSIN COUGH AND COLD LONG-ACTING HUMAN OTC DRUG LABEL 2 0031-8693 LIQUID 1 mg ORAL OTC MONOGRAPH FINAL 9 sections
Triaminic HUMAN OTC DRUG LABEL 4 0067-8116 SUSPENSION 1 mg ORAL OTC monograph final 9 sections
Good Sense Allergy Relief HUMAN OTC DRUG LABEL 1 0113-0042 TABLET 4 mg ORAL OTC monograph final 9 sections
good sense allergy relief HUMAN OTC DRUG LABEL 1 0113-0404 TABLET 4 mg ORAL OTC monograph final 8 sections
Good Sense Allergy Multi Symptom HUMAN OTC DRUG LABEL 3 0113-0476 TABLET 2 mg ORAL OTC monograph final 8 sections
good sense cold HUMAN OTC DRUG LABEL 4 0113-0903 SUSPENSION 1 mg ORAL OTC monograph final 9 sections
Allergy HUMAN OTC DRUG LABEL 3 0113-2476 TABLET 2 mg ORAL OTC monograph final 8 sections
basic care childrens cold plus flu HUMAN OTC DRUG LABEL 4 0113-7223 SUSPENSION 1 mg ORAL OTC monograph final 15 sections
TussiCaps HUMAN PRESCRIPTION DRUG LABEL 2 0187-0054 CAPSULE, EXTENDED RELEASE 4 mg ORAL ANDA 14 sections
TussiCaps HUMAN PRESCRIPTION DRUG LABEL 2 0187-0108 CAPSULE, EXTENDED RELEASE 8 mg ORAL ANDA 14 sections
Alka-Seltzer Plus Severe Cold and Flu PowerFast Fizz HUMAN OTC DRUG LABEL 4 0280-0022 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 9 sections
Alka-Seltzer Plus Severe Cold and Cough PowerFast Fizz HUMAN OTC DRUG LABEL 4 0280-0023 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 8 sections
ANTIFLU HUMAN OTC DRUG LABEL 3 0280-0044 TABLET, COATED 2 mg ORAL Export only 1 sections
Antiflu HUMAN OTC DRUG LABEL 3 0280-0045 POWDER, FOR SOLUTION 4 mg ORAL Export only 1 sections
Antiflu Kids HUMAN OTC DRUG LABEL 3 0280-0046 POWDER, FOR SOLUTION 1 mg ORAL Export only 1 sections
Alka-Seltzer Plus Cold Medicine Sparkling Original HUMAN OTC DRUG LABEL 3 0280-1400 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph not final 9 sections
Alka-Seltzer Plus Cold Orange Zest HUMAN OTC DRUG LABEL 3 0280-1510 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 17 sections
Alka-Seltzer Plus Cold Sparkling Original HUMAN OTC DRUG LABEL 3 0280-1520 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 17 sections
Alka-Seltzer Plus Multi-Symptom Cold and Cough HUMAN OTC DRUG LABEL 4 0280-1530 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 16 sections
Alka-Seltzer Plus Cold and Cough HUMAN OTC DRUG LABEL 4 0280-1555 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 16 sections
Alka-Seltzer Plus Severe Cold and Flu HUMAN OTC DRUG LABEL 4 0280-1560 TABLET, EFFERVESCENT 2 mg ORAL OTC monograph final 17 sections
Alka-Seltzer Plus Maximum Strength Cold and Cough HUMAN OTC DRUG LABEL 4 0280-1570 CAPSULE, LIQUID FILLED 2 mg ORAL OTC monograph final 17 sections
Alka-Seltzer Plus HUMAN OTC DRUG LABEL 4 0280-7055 GRANULE, EFFERVESCENT 2 mg ORAL OTC monograph final 9 sections
Childrens Plus Cold HUMAN OTC DRUG LABEL 3 0363-0026 SUSPENSION 1 mg ORAL OTC MONOGRAPH FINAL 9 sections
Childrens Plus Flu HUMAN OTC DRUG LABEL 4 0363-0030 SUSPENSION 1 mg ORAL OTC MONOGRAPH FINAL 9 sections
Childrens Plus Multi Symptom Cold HUMAN OTC DRUG LABEL 4 0363-0034 SUSPENSION 1 mg ORAL OTC MONOGRAPH FINAL 9 sections
Wal-phed HUMAN OTC DRUG LABEL 2 0363-0111 TABLET 4 mg ORAL OTC MONOGRAPH FINAL 9 sections
Childrens Plus Cough and Runny Nose HUMAN OTC DRUG LABEL 3 0363-0297 SUSPENSION 1 mg ORAL OTC MONOGRAPH FINAL 9 sections