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Dexchlorpheniramine

HCID 33036
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
25523-97-1
Standard SMILES
CN(C)CC[C@@H](c1ccc(Cl)cc1)c1ccccn1
InChIKey
SOYKEARSMXGVTM-HNNXBMFYSA-N
Molecular formula
C16H19ClN2
Average molar mass
274.79 g/mol
Monoisotopic mass
274.1236763

Overview

Dexchlorpheniramine is a chlorphenamine. It is an enantiomer of a levochlorpheniramine.

Names & identifiers

Preferred name
Dexchlorpheniramine
IUPAC
(3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
English name
Dexchlorpheniramine
Molecular formula
C16H19ClN2
Molecular weight
274.79

Names & synonyms

DEXCHLORPHENIRAMINE25523-97-1D-Chlorpheniramine(+)-ChlorpheniraminePhendextroDexclorfeniraminaDapritonFortamineIsomerinePolaraminDexchlorpheniraminumChlo-amine
Show more names
C06946MylaramineS-Chlorpheniramineexchlorpheniramine
Chlorpheniramine, d-Chlorphenamine, (s)-Chlorpheniramine, (s)-(3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine3Q9Q0B929NCHEBI:4464D-2-(p-Chloro-alpha-(2-dimethylaminoethyl)benzyl)pyridineDTXSID50180225

Database identifiers

CAS
25523-97-1
PubChem CID
33036
DTXSID
DTXSID50180225
ChEMBL
CHEMBL1201353
ChEBI
CHEBI:4464
UNII
3Q9Q0B929N
EC Number
247-073-7
Nikkaji
J19.804H

Properties

Computed structural properties

XLogP
3.4
Topological polar surface area
16.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
19
Formal charge
0
Complexity
249

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Color/FormOILY LIQUID
SolubilityWHITE CRYSTALLINE POWDER; ODORLESS; 1 G SOL IN 4 ML WATER; SOL IN ALC, CHLOROFORM; SLIGHTLY SOL IN BENZENE, ETHER /MALEATE/
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihistamines
Boiling Point142 °C @ 1.0 mm Hg /Racemate/
Melting PointCRYSTALS FROM ETHYL ACETATE; MP: 113-115 °C; SPECIFIC OPTICAL ROTATION (DIMETHYLFORMAMIDE): +44.3 DEG @ 25 °C/D, PH OF 1% SOLN 4-5 /D-FORM, MALEATE/
Optical RotationSPECIFIC OPTICAL ROTATION (DIMETHYLFORMAMIDE): +49.8 DEG @ 25 °C/D
Refractive IndexINDEX OF REFRACTION: 1.509 (ALPHA); 1.564 (BETA); 1.683 (GAMMA); OPTIC SIGN: + /MALEATE/
Collision Cross Section159.85 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Other Safety InformationIMAP assessments - 2-Pyridinepropanamine, .gamma.-(4-chlorophenyl)-N,N-dimethyl-, (S)-: Environment tier I assessment
FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Interactions · 5 items

Concurrent use /of ototoxic medications/ with antihistamines may mask the symptoms of ototoxicity such as tinnitus, dizziness, or vertigo. /Antihistamines/

Concurrent use of monoamine oxidase (MAO) inhibitors with antihistamines may prolong and intensify the anticholinergic and CNS depressant effects of antihistamines; concurrent use is not recommended. /Antihistamines/

Concurrent use /with alcohol or other CNS depression-producing medications/ may potentiate the CNS depressant effects of either these medications or antihistamines; also, concurrent use of maprotiline or tricyclic antidepressants may potentiate the anticholinergic effects of either antihistamines or these medications. /Antihistamines/

Anticholinergic effects may be potentiated when /anticholinergics or other medications with anticholinergic activity/ are used concurrently with antihistamines; patients should be advised to report occurrence of gastrointestinal problems promptly since paralytic ileus may occur with concurrent therapy. /Antihistamines/

Chemistry & industry

Pharmacology

ATC Code · 2 items

R - Respiratory system

QR - Respiratory system

Mechanism of Action · 6 items

Dexchlorpheniramine is an antihistamine that antagonizes histamine H1 receptors.

Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/

DEXCHLORPHENIRAMINE MALEATE ANTAGONIZES MANY OF CHARACTERISTIC EFFECTS OF HISTAMINE.

WHEN TESTED IN DOGS, ANTIHISTAMINIC POTENCY OF DEXTRO ISOMER WAS 100 TIMES GREATER THAN THAT OF LEVO ISOMER, & 2.5 TIMES GREATER THAN RACEMIC FORM. ON CIRCUS-MOVEMENT ATRIAL FLUTTER, LEVO FORM WAS 1.4 & 2.3 TIMES THAT OF RACEMIC & DEXTRO CMPD.

H1 antagonists inhibit most responses of smooth muscle to histamine. Antagonism of the constrictor action of histamine on respiratory smooth muscle is easily shown in vivo and in vitro. /Histamine Antagonists: H1 Antagonists/

For more Mechanism of Action (Complete) data for DEXCHLORPHENIRAMINE (7 total), please visit the HSDB record page.

Metabolism/Metabolites · 2 items

MAIN SITE OF METABOLIC TRANSFORMATION IS LIVER. /ANTIHISTAMINES/

Primarily hepatic via Cytochrome P450 (CYP450) enzymes. Half Life: 21-27 hours

MeSH Pharmacological Classification · 3 items

Agents, usually topical, that relieve itching (pruritus).

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Physicochemical properties

alpha
25 · D25 +49.8° (c = 1 in DMF)
Boiling point
142 °C · 142 °C(Press: 1.0 Torr)
Density
1.107 · 1.107±0.06 g/cm3(Predicted)
pka
9.33 · 9.33±0.28(Predicted)
FDA UNII
3 Q9Q0B929N · 3Q9Q0B929N
ATC code
6 AB02,R06AB52 · R06AB02,R06AB52
Hazardous Substances Data
25523 · 25523-97-1(Hazardous Substances Data)

Concurrent use /of other photosensitizing medications/ with antihistamines may cause additive photosensitizing effects. /Antihistamines/

Health EffectsChlorpheniramine posesses serotonergic and norepinephrinergic effects. It has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI. [Wikipedia]
Exposure RoutesWell absorbed in the gastrointestinal tract.
Toxicity SummaryChlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Human Toxicity Excerpts · 5 items

SYMPTOMATOLOGY: 1. CENTRAL NERVOUS DEPRESSION IS USUALLY DOMINANT REACTION IN ADULTS; IT IS EVIDENCED BY DROWSINESS, LETHARGY, FATIGUE, HYPNOSIS, & COMA. RELATED NERVOUS SYMPTOMS INCL VERTIGO, ATAXIA, TINNITUS, & BLURRED VISION. /ANTIHISTAMINICS/

SYMPTOMATOLOGY: 2. CENTRAL NERVOUS HYPEREXCITABILITY OFTEN FOLLOWS INITIAL SEDATION; IN CHILDREN EXCITEMENT IS OFTEN FIRST EVIDENCE OF POISONING. STIMULANT PHASE BRINGS TREMORS, ANXIETY, INSOMNIA, EXCITEMENT, HALLUCINATIONS, DELIRIUM, TOXIC PSYCHOSIS & CONVULSIONS... /ANTIHISTAMINES/

SYMPTOMATOLOGY: 3. DANGEROUS HYPERPYREXIA MAY OCCUR IN POISONED CHILDREN... 4. GASTROINTESTINAL REACTIONS INCL DRY MOUTH, ANOREXIA, NAUSEA, VOMITING, ABDOMINAL DISTRESS, CONSTIPATION, &/OR DIARRHEA. /ANTIHISTAMINICS/

SYMPTOMATOLOGY: 5. TERMINAL PHASE IS ONE OF SEVERE CENTRAL NERVOUS DEPRESSION, WITH DEATH FROM RESP ARREST OR CARDIOVASCULAR COLLAPSE. /ANTIHISTAMINICS/

For more Human Toxicity Excerpts (Complete) data for DEXCHLORPHENIRAMINE (9 total), please visit the HSDB record page.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

dexchlorpheniramine

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts · 2 items

LARGE DOSES PRODUCE CONVULSIONS IN EXPTL ANIMALS. /ANTIHISTAMINES/

SMALL DOSES OF SOME ANTIHISTAMINICS PRODUCE DEPRESSION, DROWSINESS, SALIVATION & VOMITING. /ANTIHISTAMINICS/

Populations at Special Risk · 2 items

Use is not recommended in newborn or premature infants because this age group has an increased susceptibility to anticholinergic side effects, such as central nervous system excitation, and an increased tendency toward convulsions. A paradoxical reaction characterized by hyperexcitability may occur in children taking antihistamines. /Antihistamines/

Dizziness, sedation, confusion, and hypotension may be more likely to occur in geriatric patients taking antihistamines. Geriatric patients are especially susceptible to the anticholinergic side effects, such as dryness of mouth and urinary retention (especially in males), of the antihistamines. If these side effects occur and continue or are severe, medication should probably be discontinued. /Antihistamines/

Antidote and Emergency Treatment · 1 item

THERE IS NO SPECIFIC THERAPY FOR ANTIHISTAMINE POISONING, AND TREATMENT IS ALONG GENERAL SYMPTOMATIC AND SUPPORTIVE LINES. ... SHOULD BREATHING FAIL, MECH SUPPORT OF VENTILATION OFFER SAFER AND ... EFFECTIVE MEANS OF MAINTAINING RESP THAN USE OF ANALEPTICS WHICH ARE PRONE TO INITIATE OR INTENSIFY CONVULSIVE PHASE. /ANTIHISTAMINES/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataOral LD50 (rat): 306 mg/kg Oral LD50 (mice): 130 mg/kg Oral LD50 (guinea pig): 198 mg/kg LD50: 306 mg/kg (Human) (A308)

Regulatory information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety data

Hazardous Substances Data
25523-97-1(Hazardous Substances Data)
Absorption, Distribution and Excretion · 2 items

The H1 antagonists are well absorbed from the GI tract. Following oral administration, peak plasma concn are achieved in 2 to 3 hr and effects usually last 4 to 6 hr; however, some of the drugs are much longer acting ... . /Histamine Antagonists: H1 Antagonists/

... H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /Histamine Antagonists: H1 Antagonists/

Metabolite PathwaysDexchlorpheniramine H1-Antihistamine Action

Uses & manufacturing

Uses · 5 items

ANTIHISTAMINE FOR ALLERGIC & VASOMOTOR RHINITIS (MALEATE)

ANTIHISTAMINE FOR MILD URTICARIA AND ANGIOEDEMA (MALEATE)

ANTIHISTAMINE FOR INSECT BITE REACTIONS (MALEATE)

ANTIHISTAMINE FOR PRURITUS OF ALLERGIC REACTIONS /MALEATE/

Used used in the prevention of the symptoms of allergic conditions such as rhinitis, urticaria, allergy, common cold, asthma and hay fever.

U.S. Production · 2 items

(1972) GREATER THAN 4.54X10+5 G /MALEATE/

(1975) GREATER THAN 4.54X10+5 G /MALEATE/

Consumption PatternsESSENTIALLY 100% AS AN ANTIHISTAMINE (MALEATE, 1976)
Methods of Manufacturing · 2 items

RACEMIC CHLORPHENIRAMINE...IS RESOLVED WITH AID OF D-PHENYLSUCCINIC ACID. D-ENANTIOMORPH OF BASE IS THEN LIBERATED FROM ITS D-PHENYLSUCCINATE BY TREATMENT WITH SODIUM HYDROXIDE & REACTED WITH EQUIMOLAR PORTION OF MALEIC ACID.

CONDENSATION OF 2-(P-CHLORO-ALPHA-(2-CHLOROETHYL)BENZYL)PYRIDINE WITH DIMETHYLAMINE TO PRODUCE RACEMIC CHLORPHENIRAMINE, SEPARATION OF DEXTRO ISOMER USING D-PHENYLSUCCINIC ACID, FOLLOWED BY SEQUENTIAL TREATMENT WITH SODIUM HYDROXIDE & MALEIC ACID (MALEATE)

Formulations/Preparations · 2 items

SYRUP NF: 2 MG/5 ML; TABLETS NF: 2 MG

Chlo-amine, Fortamine, Isomerine, Phenamin, Phendextro, Polaramine, Polaronil, Sensidyn /d-Form maleate/

Applications

UsesAntihistaminic.

UsesActivity of this drug is approximately twice that of chlorpheniramine. Dexchlorpheniramine is also used for allergy symptoms, rhinitis, and dermatitis.

Upstream & downstream products

Upstream raw materials

Maleic acidPotassium carbonateR-Chlorpheniramine(E)-ethyl 3-(2-pyridyl)-propenoateChloropheniramine4-Chlorophenylboronic acid

Suppliers11 total

湖北远成药业有限公司18062666904 · [email protected]
上海贺康生物技术有限公司17721021104 18939837085 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
山东子易医药有限公司13173053288 · [email protected]

Additional notes

DefinitionChEBI: Dexchlorpheniramine is a chlorphenamine. It is an enantiomer of a levochlorpheniramine.