Identification

Name
Promethazine
Accession Number
DB01069
Description

Promethazine, originally known as 3,277 R.P., is an N-dimethylaminopropyl derivative of phenothiazine that was developed in France in 1946.1 Promethazine antagonizes a variety of receptors, allowing it to be used for a number of indications including allergic reactions, pain, sedation, nausea, and vomiting.2,8,9,7,10

Promethazine was granted FDA approval before 29 March 1951.11,12

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 284.419
Monoisotopic: 284.13471934
Chemical Formula
C17H20N2S
Synonyms
  • (2-dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine
  • 10-(2-Dimethylaminopropyl)phenothiazine
  • 10-[2-(dimethylamino)propyl]phenothiazine
  • N-(2'-dimethylamino-2'-methyl)ethylphenothiazine
  • N,N,alpha-trimethyl-10H-phenothiazine-10-ethanamine
  • N,N,α-trimethyl-10H-phenothiazine-10-ethanamine
  • Proazamine
  • Prometazina
  • Promethazine
  • Promethazinum
External IDs
  • Lilly 1516

Pharmacology

Indication

Promethazine tablets and suppositories are indicated to treat rhinitis, allergic conjunctivitis, allergic reactions to blood or plasma, dermographism, anaphylactic reactions, sedation, nausea, vomiting, pain, motion sickness, and allergic skin reactions.2,12 Promethazine cough syrup with phenylephrine and codeine is indicated to relieve cough and upper respiratory symptoms, and nasal congestion associated with allergy or the common cold.13

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Promethazine is is a histamine H1 antagonist that can be used for it's ability to induce sedation, reduce pain, and treat allergic reactions.12 Promethazine's effects generally last 4-6h but can last up to 12h.12 Patients should be counselled regarding CNS and respiratory depression, reduce seizure threshold, and bone marrow depression.12

Mechanism of action

Promethazine is a an antagonist of histamine H1, post-synaptic mesolimbic dopamine, alpha adrenergic, muscarinic, and NMDA receptors.2,8,9 The antihistamine action is used to treat allergic reactions.7 Antagonism of muscarinic and NMDA receptors contribute to its use as a sleep aid, as well as for anxiety and tension.9 Antagonism of histamine H1, muscarinic, and dopamine receptors in the medullary vomiting center make promethazine useful in the treatment of nausea and vomiting.10

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
UDopamine D2 receptor
antagonist
Humans
UMuscarinic acetylcholine receptor M1
antagonist
Humans
UMuscarinic acetylcholine receptor M2
antagonist
Humans
UMuscarinic acetylcholine receptor M3
antagonist
Humans
UMuscarinic acetylcholine receptor M4
antagonist
Humans
UMuscarinic acetylcholine receptor M5
antagonist
Humans
UAlpha adrenergic receptor
antagonist
Humans
UCalmodulin
inhibitor
Humans
UHistamine H2 receptor
antagonist
Humans
UP2 Purinoceptors
inhibitor
UVoltage-gated sodium channel alpha subunit
inhibitor
Humans
UVoltage-gated Potassium Channels
inducer
Absorption

A 25mg dose of intramuscular promethazine reaches a Cmax of 22ng/mL.4 Intravenous promethazine reaches a Cmax of 10.0ng/mL, with a Tmax of 4-10h, and an AUC of 14,466ng*h/mL.4 Oral promethazine is only 25% bioavailable due to first pass metabolism.4 Oral promethazine reaches a Cmax of 2.4-18.0ng/mL, with a Tmax of 1.5-3h, and an AUC of 11,511ng*h/mL.4

Volume of distribution

The volume of distribution of promethazine is approximately 970L or 30L/kg.4

Protein binding

Promethazine is 93% protein bound in serum,5 mostly to albumin.6

Metabolism

Promethazine is predominantly metabolized to promethazine sulfoxide, and minorly to desmethylpromethazine and a hydroxy metabolite.3,4 Hydroxylation of promethazine is predominantly mediated by CYP2D6.3

Hover over products below to view reaction partners

Route of elimination

An intravenous dose of promethazine is 0.64% eliminated in the urine as the unchanged parent drug, 0.02-2.02% in the urine as desmethylpromethazine, 10% in the urine as promethazine sulfoxide.4

Half-life

The elimination half life of promethazine is approximately 12-15h.4

Clearance

The intravenous clearance of promethazine is approximately 1.14L/min.4 The renal clearance of promethazine is 5.9mL/min and the renal clearance of promethazine sulfoxide is 90.4mL/min.4

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The intraperitoneal LD50 in rats is 170mg/kg and in mice is 160mg/kg.14 The subcutaneous LD50 in rats is 400mg/kg and in mice is 240mg/kg.14 The oral LD50 in mice is 255mg/kg.14

Patients experiencing an overdose of promethazine may present with mild central nervous system and cardiovascular depression, hypotension, respiratory depression, unconciousness, hyperreflexia, hypertonia, ataxia, athetosis, extensor-plantar reflexes, convulsions, dry mouth, flushing, gastrointestinal symptoms, and fixed, dilated pupils.12 Treat overdoses with symptomatic and supportive treatment, which may include activated charcoal, sodium sulfate, magnesium sulfate, controlled ventilation, diazepam, intravenous fluids, vasopressors, norepinephrine, phenylephrine, anticholinergic antiparkinsonian agents, diphenhydramine, barbiturates, or oxygen.12

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Promethazine H1-Antihistamine ActionDrug action
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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Promethazine which could result in a higher serum level.
AbametapirThe serum concentration of Promethazine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Promethazine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Promethazine can be decreased when combined with Abiraterone.
AcarboseAcarbose may decrease the excretion rate of Promethazine which could result in a higher serum level.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Promethazine.
AceclofenacAceclofenac may decrease the excretion rate of Promethazine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Promethazine which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Promethazine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Promethazine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol. Alcohol may increase the sedation caused by promethazine.

Products

Product Ingredients
IngredientUNIICASInChI Key
Promethazine hydrochlorideR61ZEH7I1I58-33-3XXPDBLUZJRXNNZ-UHFFFAOYSA-N
Product Images
International/Other Brands
Avomine / Fargan / Farganesse / Lergigan / Prothiazine / Receptozine / Romergan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PhenerganTablet25 mg/1OralWyeth Ltd.1951-05-012008-06-30Us
PhenerganSuppository25 mg/1RectalWyeth Ltd.1951-05-012008-06-30Us
PhenerganSuppository12.5 mg/1RectalWyeth Ltd.1951-05-012008-06-30Us
PhenerganTablet12.5 mg/1OralWyeth Ltd.1951-05-012008-06-03Us
PhenerganTablet50 mg/1OralWyeth Ltd.1951-05-012008-06-30Us
PhenerganSuppository50 mg/1RectalWyeth Ltd.1951-05-012008-06-30Us
Phenergan Injectable 25mg/mlSolutionIntramuscular; IntravenousAventis Pharma Ltd.1949-12-312005-08-01Canada
Promethazine HClInjection, solution0.5 mg/1mLIntravenousCantrell Drug Company2014-05-29Not applicableUs
Promethazine HClSyrup6.25 mg/5mLOralANI Pharmaceuticals, Inc.2008-05-022008-05-02Us
Promethazine HClInjection50 mg/1mLIntramuscular; IntravenousWatson Pharmaceuticals2006-04-05Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PhenadozSuppository12.5 mg/1RectalPd Rx Pharmaceuticals, Inc.2003-06-242018-02-08Us
PhenadozSuppository12.5 mg/1RectalA-S Medication Solutions2015-03-16Not applicableUs
PhenadozSuppository25 mg/1RectalActavis Pharma Company2013-04-032016-05-31Us
PhenadozSuppository25 mg/1RectalA-S Medication Solutions2015-02-17Not applicableUs
PhenadozSuppository25 mg/1RectalRemedy Repack2016-10-202016-10-20Us
PhenadozSuppository12.5 mg/1RectalActavis Pharma, Inc.2015-03-162021-02-28Us
PhenadozSuppository12.5 mg/1RectalPaddock Laboratories, Inc.2003-06-242016-11-30Us
PhenadozSuppository12.5 mg/1RectalActavis Pharma Company2013-02-122016-11-30Us
PhenadozSuppository25 mg/1RectalActavis Pharma, Inc.2015-02-172022-01-30Us
PhenadozSuppository25 mg/1RectalPaddock Laboratories, Inc.2003-06-242016-11-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Histantil Tab 25mgTabletOralPharmascience Inc1983-12-31Not applicableCanada
Histantil Tab 50mgTabletOralPharmascience Inc1983-12-31Not applicableCanada
Phenergan 50TabletOralColumbia Laboratories1996-12-312002-07-17Canada
Phenergan Cream 2%CreamTopicalColumbia Laboratories1996-07-302007-07-24Canada
Phenergan Cream 2%CreamTopicalRhone Poulenc Rorer1993-12-311997-08-13Canada
Phenergan Syrup 10mg/5mlSyrupOralRhone Poulenc Rorer1993-12-311996-09-09Canada
Phenergan Tablet 10mgTabletOralRhone Poulenc Rorer1993-12-311997-08-13Canada
Phenergan Tablet 25mgTabletOralNovartis1996-12-311999-07-21Canada
Phenergan Tablet 25mgTabletOralRhone Poulenc Rorer1993-12-311997-08-13Canada
Phenergan Tablet 50mgTabletOralRhone Poulenc Rorer1992-12-311997-08-13Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dextromethorphan Hydrobromide and Promethazine HydrochloridePromethazine hydrochloride (6.25 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL)SyrupOralRemedy Repack2013-12-022014-12-02Us
Dextromethorphan Hydrobromide and Promethazine HydrochloridePromethazine hydrochloride (6.25 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL)SyrupOralProficient Rx LP1985-01-04Not applicableUs
Dextromethorphan Hydrobromide and Promethazine HydrochloridePromethazine hydrochloride (6.25 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL)SyrupOralAtlantic Biologicals Corps.1985-01-04Not applicableUs
Promatussin DM Adult Formula SyrPromethazine hydrochloride (6.25 mg) + Dextromethorphan hydrobromide (15 mg) + Pseudoephedrine hydrochloride (60 mg)SyrupOralWyeth Ayerst Canada Inc.1993-12-311996-09-10Canada
Promatussin DM Children FormulaPromethazine hydrochloride (3.125 mg) + Dextromethorphan hydrobromide (7.5 mg) + Pseudoephedrine hydrochloride (30 mg)LiquidOralWyeth Ltd.1981-12-311996-09-10Canada
Prometh with CodeinePromethazine hydrochloride (6.25 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL)SyrupOralRebel Distributors1984-10-31Not applicableUs
Prometh with CodeinePromethazine hydrochloride (6.25 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL)SyrupOralRemedy Repack2013-07-082013-07-09Us
Prometh with CodeinePromethazine hydrochloride (6.25 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL)SyrupOralbryant ranch prepack1990-09-302012-06-01Us
Prometh with CodeinePromethazine hydrochloride (6.25 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL)SyrupOralActavis Pharma Company1990-09-302015-06-30Us
Prometh with DextromethorphanPromethazine hydrochloride (6.25 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL)SyrupOralActavis Pharma Company2007-01-032011-05-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Meperidine Hcl and Promethazine HclPromethazine hydrochloride (25 mg/1) + Meperidine hydrochloride (50 mg/1)CapsuleOralPhysicians Total Care, Inc.2004-09-032013-01-15Us
Meperidine Hydrochloride and Promethazine HydrochloridePromethazine hydrochloride (25 mg/1) + Meperidine hydrochloride (50 mg/1)CapsuleOralEci Pharmaceuticals Llc2013-02-192018-06-30Us
Promethazine HClPromethazine hydrochloride (0.5 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-05-29Not applicableUs
Promethazine HClPromethazine hydrochloride (0.625 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-05-27Not applicableUs
Promethazine HClPromethazine hydrochloride (1 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-05-272017-12-06Us

Categories

ATC Codes
R06AD52 — Promethazine, combinationsD04AA10 — PromethazineV03AB05 — Prednisolone and promethazineR06AD02 — Promethazine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / Benzenoids / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, tertiary amine (CHEBI:8461)

Chemical Identifiers

UNII
FF28EJQ494
CAS number
60-87-7
InChI Key
PWWVAXIEGOYWEE-UHFFFAOYSA-N
InChI
InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
IUPAC Name
dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
SMILES
CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C

References

Synthesis Reference
US2530451
General References
  1. HALPERN BN, HAMBURGER J: A new synthetic anti-histamine substance derived from phenothiazine; phenergan, 3,277 R.P. Can Med Assoc J. 1948 Oct;59(4):322-6. [PubMed:18886695]
  2. Southard BT, Al Khalili Y: Promethazine . [PubMed:31335081]
  3. Nakamura K, Yokoi T, Inoue K, Shimada N, Ohashi N, Kume T, Kamataki T: CYP2D6 is the principal cytochrome P450 responsible for metabolism of the histamine H1 antagonist promethazine in human liver microsomes. Pharmacogenetics. 1996 Oct;6(5):449-57. [PubMed:8946477]
  4. Taylor G, Houston JB, Shaffer J, Mawer G: Pharmacokinetics of promethazine and its sulphoxide metabolite after intravenous and oral administration to man. Br J Clin Pharmacol. 1983 Mar;15(3):287-93. doi: 10.1111/j.1365-2125.1983.tb01501.x. [PubMed:6849764]
  5. Cantisani C, Ricci S, Grieco T, Paolino G, Faina V, Silvestri E, Calvieri S: Topical promethazine side effects: our experience and review of the literature. Biomed Res Int. 2013;2013:151509. doi: 10.1155/2013/151509. Epub 2013 Nov 19. [PubMed:24350243]
  6. He LL, Wang ZX, Wang YX, Liu XP, Yang YJ, Gao YP, Wang X, Liu B, Wang X: Studies on the interaction between promethazine and human serum albumin in the presence of flavonoids by spectroscopic and molecular modeling techniques. Colloids Surf B Biointerfaces. 2016 Sep 1;145:820-829. doi: 10.1016/j.colsurfb.2016.06.001. Epub 2016 Jun 2. [PubMed:27315330]
  7. Authors unspecified: Promethazine . [PubMed:31643746]
  8. Smith HS, Cox LR, Smith BR: Dopamine receptor antagonists. Ann Palliat Med. 2012 Jul;1(2):137-42. doi: 10.3978/j.issn.2224-5820.2012.07.09. [PubMed:25841474]
  9. Adolph O, Koster S, Georgieff M, Georgieff EM, Moulig W, Fohr KJ: Promethazine inhibits NMDA-induced currents - new pharmacological aspects of an old drug. Neuropharmacology. 2012 Aug;63(2):280-91. doi: 10.1016/j.neuropharm.2012.03.006. Epub 2012 Apr 7. [PubMed:22507664]
  10. Flake ZA, Linn BS, Hornecker JR: Practical selection of antiemetics in the ambulatory setting. Am Fam Physician. 2015 Mar 1;91(5):293-6. [PubMed:25822385]
  11. AVERY JL: Treatment of enterobiasis with one oral dose of promethazine hydrochloride. J Am Med Assoc. 1956 Jun 23;161(8):681-3. doi: 10.1001/jama.1956.02970080011004. [PubMed:13318985]
  12. FDA Approved Drug Products: Phenergran Promethazine Oral Tablets (Discontinued) [Link]
  13. FDA Approved Drug Products: Promethazine with Phenylephrine and Codeine Oral Syrup [Link]
  14. Cayman Chemical: Promethazine MSDS [Link]
Human Metabolome Database
HMDB0015202
KEGG Drug
D00494
KEGG Compound
C07404
PubChem Compound
4927
PubChem Substance
46507798
ChemSpider
4758
BindingDB
50017696
RxNav
8745
ChEBI
8461
ChEMBL
CHEMBL643
Therapeutic Targets Database
DAP000334
PharmGKB
PA451128
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Promethazine
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics
  • 04:04.12 — Phenothiazine Derivatives
FDA label
Download (93.4 KB)
MSDS
Download (74.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceVestibular1
4CompletedPreventionNausea / Post Operative Nausea and Vomiting (PONV)1
4CompletedPreventionPost Operative Nausea and Vomiting (PONV)1
4CompletedTreatmentAggressive reaction / Agitation / Psychiatric Emergency1
4CompletedTreatmentChronic Hepatitis C Infection With Hepatic Coma / Hepatic Failure / Hepatic Impairment1
4CompletedTreatmentNausea / Vomiting1
4CompletedTreatmentSnake Bites1
4Unknown StatusTreatmentBack Pain Lower Back1
3CompletedPreventionNausea / Pain / Vomiting1
3CompletedTreatmentAggressive reaction / Psychotic Disorder NOS1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Baxter International Inc.
  • Bioniche Pharma
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Cadila Healthcare Ltd.
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Century Pharmaceuticals Inc.
  • Clint Pharmaceutical Inc.
  • Comprehensive Consultant Services Inc.
  • Consolidated Midland Corp.
  • Corepharma LLC
  • Dee Stevens and Son Feeder
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Ebewe Pharma
  • G & W Labs
  • General Injectables and Vaccines Inc.
  • Global Pharmaceuticals
  • Goldline Laboratories Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hi Tech Pharmacal Co. Inc.
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Impax Laboratories Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • KVK-Tech Inc.
  • Lake Erie Medical and Surgical Supply
  • Lark Pharmaceuticals Inc.
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Martica Enterprises Inc.
  • Martin Surgical Supply
  • Mckesson Corp.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Nubenco Enterprises Inc.
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaceutical Association
  • Pharmacy Service Center
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
CapsuleOral
Injection, solutionIntramuscular50 mg/1mL
SuppositoryRectal50 mg/1
CreamTopical
SolutionIntramuscular; Intravenous
SyrupOral
TabletOral
Tablet, film coatedOral10 MG
Tablet, film coatedOral100 MG
Tablet, film coatedOral25 MG
Tablet, film coatedOral50 MG
Tablet, film coatedOral75 MG
InjectionIntramuscular50 mg/1mL
InjectionIntramuscular; Intravenous25 mg/1mL
InjectionIntramuscular; Intravenous50 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
Injection, solutionIntravenous0.625 mg/1mL
Injection, solutionIntravenous1 mg/1mL
SolutionOral
InjectionIntramuscular25 mg/1mL
Injection, solutionIntramuscular25 mg/1
Injection, solutionIntramuscular; Intravenous25 mg/1mL
Injection, solutionIntramuscular; Intravenous50 mg/1mL
PowderNot applicable1 g/1g
SolutionOral6.25 mg/5mL
SuppositoryRectal12.5 mg/1
SuppositoryRectal25 mg/1
SyrupOral6.25 mg/5mL
TabletOral12.5 mg/1
TabletOral25 mg/301
TabletOral25 mg/1
TabletOral50 mg/1
LiquidIntramuscular; Intravenous
LiquidOral
SyrupOral
Tablet, sugar coatedOral25 MG
Prices
Unit descriptionCostUnit
Promethegan 12 50 mg Suppository Box101.64USD box
Phenergan 12 50 mg Suppository Box80.16USD box
Phenergan 12 25 mg Suppository Box62.59USD box
Promethegan 12 25 mg Suppository Box62.27USD box
Promethazine HCl 12 50 mg Suppository Box60.94USD box
Phenergan 12 12.5 mg Suppository Box54.58USD box
Phenergan 25 mg suppository8.32USD suppository
Promethegan 50 mg suppository8.14USD suppository
Phenergan 12.5 mg suppository7.94USD suppository
Phenergan 50 mg suppository7.39USD suppository
Promethazine 50 mg suppository4.88USD suppository
Promethegan 25 mg suppository4.62USD suppository
Phenadoz 25 mg suppository4.45USD suppository
Promethazine 25 mg suppository4.32USD suppository
Promethegan 12.5 mg suppository4.02USD suppository
Promethazine HCl 12.5 mg Suppository4.0USD suppository
Phenadoz 12.5 mg suppository3.89USD suppository
Phenergan 25 mg/ml ampul3.84USD ml
Promethazine 12.5 mg suppository3.82USD suppository
Phenergan 50 mg/ml ampul3.68USD ml
Promethazine HCl 50 mg/ml Solution 1ml Ampule2.8USD ampule
Promethazine 50 mg/ml ampul2.25USD ml
Promethazine hcl powder2.14USD g
Promethazine 25 mg/ml ampul1.1USD ml
Promethazine 25 mg/ml1.06USD ml
Promethazine HCl 50 mg tablet0.81USD tablet
Promethazine 50 mg tablet0.78USD tablet
Promethazine HCl 25 mg tablet0.73USD tablet
Phenergan 25 mg tablet0.62USD tablet
Promethazine 25 mg tablet0.51USD tablet
Promethazine 12.5 mg tablet0.49USD tablet
Promethazine-DM 6.25-15 mg/5ml Syrup0.18USD ml
Promethazine HCl 6.25 mg/5ml Syrup0.11USD ml
Promethazine VC Plain 6.25-5 mg/5ml Syrup0.09USD ml
Promethazine-Codeine 6.25-10 mg/5ml Syrup0.06USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)60 °CPhysProp
boiling point (°C)190-192 °C at 3.00E+00 mm HgPhysProp
water solubility15.6 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.81HANSCH,C ET AL. (1995)
logS-4.26ADME Research, USCD
pKa9.1SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0245 mg/mLALOGPS
logP4.52ALOGPS
logP4.29ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.5 m3·mol-1ChemAxon
Polarizability32.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9832
Blood Brain Barrier+0.9855
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8157
P-glycoprotein inhibitor IInhibitor0.8408
P-glycoprotein inhibitor IINon-inhibitor0.6473
Renal organic cation transporterInhibitor0.5156
CYP450 2C9 substrateNon-substrate0.7736
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5338
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.567
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9088
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6959 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9786
hERG inhibition (predictor II)Inhibitor0.7661
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.88 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - CI-BGC-MSsplash10-000i-0090000000-f1fe9756bed13819bbb4
GC-MS Spectrum - EI-BGC-MSsplash10-00di-9000000000-abbdf5514dccef4821b2
GC-MS Spectrum - EI-BGC-MSsplash10-00di-9100000000-9bef9a6b83d662fc7e2c
GC-MS Spectrum - CI-BGC-MSsplash10-0079-8290000000-fe5d6b4e9f62b7270798
Mass Spectrum (Electron Ionization)MSsplash10-00di-9210000000-7167670dff3395a6ade2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000j-0690000000-0b4dfbac9712d2e36046
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-9220000000-9d761be1437f10dcc94b

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Suzuki A, Yasui-Furukori N, Mihara K, Kondo T, Furukori H, Inoue Y, Kaneko S, Otani K: Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol. Ther Drug Monit. 2003 Apr;25(2):192-6. [PubMed:12657913]
  3. Smith BN, Armstrong WE: Histamine enhances the depolarizing afterpotential of immunohistochemically identified vasopressin neurons in the rat supraoptic nucleus via H1-receptor activation. Neuroscience. 1993 Apr;53(3):855-64. [PubMed:8098142]
  4. Miller RA, Tu AT: Factors in snake venoms that increase capillary permeability. J Pharm Pharmacol. 1989 Nov;41(11):792-4. [PubMed:2576052]
  5. Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [PubMed:3011460]
  6. Ikeda H, Kubo N, Nakamura A, Harada N, Minamino M, Yamashita T: Histamine-induced calcium released from cultured human mucosal microvascular endothelial cells from nasal inferior turbinate. Acta Otolaryngol. 1997 Nov;117(6):864-70. [PubMed:9442829]
  7. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Southard BT, Al Khalili Y: Promethazine . [PubMed:31335081]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 Da
References
  1. Cohen ME, Sharp GW, Donowitz M: Suggestion of a role for calmodulin and phosphorylation in regulation of rabbit ileal electrolyte transport: effects of promethazine. Am J Physiol. 1986 Nov;251(5 Pt 1):G710-7. [PubMed:3022601]
  2. Scott JA, Khaw BA, Fallon JT, Locke E, Rabito CA, Peto CA, Homcy CJ: The effect of phenothiazines upon maintenance of membrane integrity in the cultured myocardial cell. J Mol Cell Cardiol. 1986 Dec;18(12):1243-54. [PubMed:3820316]
  3. Lohr KM, Feix JB, Kurth C: Chlorpromazine inhibits neutrophil chemotaxis beyond the chemotactic receptor-ligand interaction. J Infect Dis. 1984 Nov;150(5):643-52. [PubMed:6092486]
  4. DiPaola M, Keith CH, Feldman D, Tycko B, Maxfield FR: Loss of alpha 2-macroglobulin and epidermal growth factor surface binding induced by phenothiazines and naphthalene sulfonamides. J Cell Physiol. 1984 Feb;118(2):193-202. [PubMed:6319437]
  5. Luchowski EM, Yousif F, Triggle DJ, Maurer SC, Sarmiento JG, Janis RA: Effects of metal cations and calmodulin antagonists on [3H] nitrendipine binding in smooth and cardiac muscle. J Pharmacol Exp Ther. 1984 Sep;230(3):607-13. [PubMed:6433001]
  6. Baig AM, Katyara P, Rajabali MN, Khaleeq A, Nazim F, Lalani S: Neuroleptic Drug Targets a Brain-Eating Amoeba: Effects of Promethazine on Neurotropic Acanthamoeba castellanii. ACS Chem Neurosci. 2019 Jun 19;10(6):2868-2876. doi: 10.1021/acschemneuro.9b00100. Epub 2019 May 15. [PubMed:30977998]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
Molecular Weight
40097.65 Da
References
  1. Dick W, Lorenz W, Heintz D, Sitter H, Doenicke A: [Histamine release during induction of combination anesthesia using nalbuphine or fentanyl. Modulation of the reaction by premedication with promethazine/pethidine]. Anaesthesist. 1992;41(5):239-47. [PubMed:1377455]
Kind
Protein group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Receptor for lysophosphatidic acid (LPA), a mediator of diverse cellular activities. Transduces a signal by increasing the intracellular calcium ions and by stimulating adenylyl cyclase activity. The rank order of potency for agonists of this receptor is 1-oleoyl- > 1-stearoyl- > 1-palmitoyl- > 1-myristoyl- > 1-alkyl- > 1-alkenyl-LPA.
Specific Function
G protein-coupled receptor activity

Components:
References
  1. Cantisani C, Ricci S, Grieco T, Paolino G, Faina V, Silvestri E, Calvieri S: Topical promethazine side effects: our experience and review of the literature. Biomed Res Int. 2013;2013:151509. doi: 10.1155/2013/151509. Epub 2013 Nov 19. [PubMed:24350243]
  2. Horvat A, Orlic T, Banjac A, Momic T, Petrovic S, Demajo M: Inhibition of rat brain ecto-atpase activity by various drugs. Gen Physiol Biophys. 2006 Mar;25(1):91-105. [PubMed:16714778]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...

Components:
References
  1. Cantisani C, Ricci S, Grieco T, Paolino G, Faina V, Silvestri E, Calvieri S: Topical promethazine side effects: our experience and review of the literature. Biomed Res Int. 2013;2013:151509. doi: 10.1155/2013/151509. Epub 2013 Nov 19. [PubMed:24350243]
  2. Tanaka H, Habuchi Y, Nishimura M, Sato N, Watanabe Y: Blockade of Na+ current by promethazine in guinea-pig ventricular myocytes. Br J Pharmacol. 1992 Aug;106(4):900-5. doi: 10.1111/j.1476-5381.1992.tb14432.x. [PubMed:1327391]
Kind
Protein group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inducer
General Function
Voltage-gated potassium channel activity
Specific Function
Voltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain and the central nervous system, but also in the kidney (PubMed:1990381...

Components:
NameUniProt ID
Potassium voltage-gated channel subfamily A member 1Q09470
Potassium voltage-gated channel subfamily A member 10Q16322
Potassium voltage-gated channel subfamily A member 2P16389
Potassium voltage-gated channel subfamily A member 3P22001
Potassium voltage-gated channel subfamily A member 4P22459
Potassium voltage-gated channel subfamily A member 5P22460
Potassium voltage-gated channel subfamily A member 6P17658
Potassium voltage-gated channel subfamily B member 1Q14721
Potassium voltage-gated channel subfamily B member 2Q92953
Potassium voltage-gated channel subfamily C member 1P48547
Potassium voltage-gated channel subfamily C member 2Q96PR1
Potassium voltage-gated channel subfamily C member 3Q14003
Potassium voltage-gated channel subfamily C member 4Q03721
Potassium voltage-gated channel subfamily D member 1Q9NSA2
Potassium voltage-gated channel subfamily D member 2Q9NZV8
Potassium voltage-gated channel subfamily D member 3Q9UK17
Potassium voltage-gated channel subfamily E member 1P15382
Potassium voltage-gated channel subfamily E member 2Q9Y6J6
Potassium voltage-gated channel subfamily E member 3Q9Y6H6
Potassium voltage-gated channel subfamily E member 4Q8WWG9
Potassium voltage-gated channel subfamily E regulatory beta subunit 5Q9UJ90
Potassium voltage-gated channel subfamily F member 1Q9H3M0
Potassium voltage-gated channel subfamily G member 1Q9UIX4
Potassium voltage-gated channel subfamily G member 2Q9UJ96
Potassium voltage-gated channel subfamily G member 3Q8TAE7
Potassium voltage-gated channel subfamily G member 4Q8TDN1
Potassium voltage-gated channel subfamily H member 1O95259
Potassium voltage-gated channel subfamily H member 2Q12809
Potassium voltage-gated channel subfamily H member 3Q9ULD8
Potassium voltage-gated channel subfamily H member 4Q9UQ05
Potassium voltage-gated channel subfamily H member 5Q8NCM2
Potassium voltage-gated channel subfamily H member 6Q9H252
Potassium voltage-gated channel subfamily H member 7Q9NS40
Potassium voltage-gated channel subfamily H member 8Q96L42
Potassium voltage-gated channel subfamily KQT member 1P51787
Potassium voltage-gated channel subfamily KQT member 2O43526
Potassium voltage-gated channel subfamily KQT member 3O43525
Potassium voltage-gated channel subfamily KQT member 4P56696
Potassium voltage-gated channel subfamily KQT member 5Q9NR82
Potassium voltage-gated channel subfamily S member 1Q96KK3
Potassium voltage-gated channel subfamily S member 3Q9BQ31
Potassium voltage-gated channel subfamily V member 1Q6PIU1
Potassium voltage-gated channel subfamily V member 2Q8TDN2
Voltage-gated potassium channel subunit beta-1Q14722
Voltage-gated potassium channel subunit beta-2Q13303
References
  1. Cantisani C, Ricci S, Grieco T, Paolino G, Faina V, Silvestri E, Calvieri S: Topical promethazine side effects: our experience and review of the literature. Biomed Res Int. 2013;2013:151509. doi: 10.1155/2013/151509. Epub 2013 Nov 19. [PubMed:24350243]
  2. Galeotti N, Ghelardini C, Bartolini A: The role of potassium channels in antihistamine analgesia. Neuropharmacology. 1999 Dec;38(12):1893-901. doi: 10.1016/s0028-3908(99)00068-4. [PubMed:10608284]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Platts SH, Shi SJ, Meck JV: Akathisia with combined use of midodrine and promethazine. JAMA. 2006 May 3;295(17):2000-1. [PubMed:16670408]
  2. Nakamura K, Yokoi T, Inoue K, Shimada N, Ohashi N, Kume T, Kamataki T: CYP2D6 is the principal cytochrome P450 responsible for metabolism of the histamine H1 antagonist promethazine in human liver microsomes. Pharmacogenetics. 1996 Oct;6(5):449-57. [PubMed:8946477]
  3. He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [PubMed:11936702]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Potential CYP2B6 Substrates, Inhibitors, Inudcers (https://ctep.cancer.gov/protocoldevelopment/docs/cyp2b6.doc) [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Only exerts an inhibitory effect at high concentrations not normally observed in plasma.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [PubMed:11936702]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. He LL, Wang ZX, Wang YX, Liu XP, Yang YJ, Gao YP, Wang X, Liu B, Wang X: Studies on the interaction between promethazine and human serum albumin in the presence of flavonoids by spectroscopic and molecular modeling techniques. Colloids Surf B Biointerfaces. 2016 Sep 1;145:820-829. doi: 10.1016/j.colsurfb.2016.06.001. Epub 2016 Jun 2. [PubMed:27315330]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [PubMed:11082465]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Kock K, Ferslew BC, Netterberg I, Yang K, Urban TJ, Swaan PW, Stewart PW, Brouwer KL: Risk factors for development of cholestatic drug-induced liver injury: inhibition of hepatic basolateral bile acid transporters multidrug resistance-associated proteins 3 and 4. Drug Metab Dispos. 2014 Apr;42(4):665-74. doi: 10.1124/dmd.113.054304. Epub 2013 Oct 23. [PubMed:24154606]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Kock K, Ferslew BC, Netterberg I, Yang K, Urban TJ, Swaan PW, Stewart PW, Brouwer KL: Risk factors for development of cholestatic drug-induced liver injury: inhibition of hepatic basolateral bile acid transporters multidrug resistance-associated proteins 3 and 4. Drug Metab Dispos. 2014 Apr;42(4):665-74. doi: 10.1124/dmd.113.054304. Epub 2013 Oct 23. [PubMed:24154606]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2020 22:18

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