A phenothiazine with actions similar to chlorpromazine but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic. Promazine is not approved for use in the United States.

Structure

Similar Structures

Synonyms

10-(3-(Dimethylamino)propyl)phenothiazine
N-(3-Dimethylaminopropyl)phenothiazine
N-Dimethylamino-1-methylethyl thiodiphenylamine
N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine
Promazin
Promazina
Promazine
Promazinum

External IDs

A 145 / RP 3276 / Wy 1094

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Promazine hydrochloride	U16EOR79U4	53-60-1	JIVSXRLRGOICGA-UHFFFAOYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Promazine HCl Inj 50mg/ml	Liquid	50 mg	Intramuscular; Intravenous	Abbott	1981-12-31	2008-06-06

International/Other Brands

Combelen / Prazine (Pliva) / Sparine / Talofen (Abbott)

Categories

UNII

O9M39HTM5W

CAS number

58-40-2

Weight

Average: 284.419
Monoisotopic: 284.13471934

Chemical Formula

C₁₇H₂₀N₂S

InChI Key

ZGUGWUXLJSTTMA-UHFFFAOYSA-N

InChI

InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3

IUPAC Name

dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine

SMILES

CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12

Pharmacology

Indication

Used as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly.

Pharmacodynamics

Promazine belongs to a group of medications known as the phenothiazine antipsychotics. It acts by blocking a variety of receptors in the brain, particularly dopamine receptors. Dopamine is involved in transmitting signals between brain cells. When there is an excess amount of dopamine in the brain it causes over-stimulation of dopamine receptors. These receptors normally act to modify behaviour and over-stimulation may result in psychotic illness. Promazine hydrochloride blocks these receptors and stops them becoming over-stimulated, thereby helping to control psychotic illness. Promazine has weak extrapyramidal and autonomic side effects which lead to its use in the elderly, for restless or psychotic patients. Its anti-psychotic effect is also weaker and it is not useful in general psychiatry.

Mechanism of action

Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine.

Target	Actions	Organism
AD(2) dopamine receptor	antagonist	Humans
U5-hydroxytryptamine receptor 2A	antagonist	Humans
U5-hydroxytryptamine receptor 2C	antagonist	Humans
UD(1A) dopamine receptor	antagonist	Humans
UD(4) dopamine receptor	antagonist	Humans
UMuscarinic acetylcholine receptor M4	antagonist	Humans
UMuscarinic acetylcholine receptor M2	antagonist	Humans
UMuscarinic acetylcholine receptor M3	antagonist	Humans
UMuscarinic acetylcholine receptor M1	antagonist	Humans
UAlpha-1B adrenergic receptor	antagonist	Humans
UMuscarinic acetylcholine receptor M5	antagonist	Humans
UAlpha-1A adrenergic receptor	antagonist	Humans
UHistamine H1 receptor	antagonist	Humans
UAlpha-1D adrenergic receptor	antagonist	Humans

Absorption

Absorption may be erratic and peak plasma concentrations show large interindividual differences.

Volume of distribution

Not Available

Protein binding

94%

Metabolism

Hepatic, primarily to N-desmethylpromazine and promazine sulfoxide.

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Side effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Promazine.
(S)-Warfarin	The risk or severity of adverse effects can be increased when Promazine is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The risk or severity of hypertension can be increased when Promazine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazole	The risk or severity of hypertension can be increased when Promazine is combined with 1-benzylimidazole.
1,10-Phenanthroline	The therapeutic efficacy of Promazine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamine	The therapeutic efficacy of Promazine can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The therapeutic efficacy of Promazine can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Promazine.
3,5-Dinitrocatechol	The therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Promazine.
4-Bromo-2,5-dimethoxyamphetamine	The therapeutic efficacy of Promazine can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.

Food Interactions

Not Available

References

Synthesis Reference

US2519886

General References

Cubala WJ, Jakuszkowiak-Wojten K, Burkiewicz A, Wronska A: Promazine in the treatment of delusional parasitosis. Psychiatr Danub. 2011 Jun;23(2):198-9. [PubMed:21685861]

External Links

Human Metabolome Database: HMDB0014564
KEGG Drug: D08430
KEGG Compound: C07379
PubChem Compound: 4926
PubChem Substance: 46504504
ChemSpider: 4757
BindingDB: 67545
ChEBI: 8459
ChEMBL: CHEMBL564
Therapeutic Targets Database: DAP000430
PharmGKB: PA451126
HET: P2Z
Wikipedia: Promazine

ATC Codes

N05AA03 — Promazine

PDB Entries

4ma7

MSDS

Download (75.4 KB)

Clinical Trials

Clinical Trials: Not Available

Pharmacoeconomics

Manufacturers

Wyeth ayerst laboratories
Watson laboratories inc
Baxter healthcare corp anesthesia critical care
Apothecon sub bristol myers squibb co
Apothecon inc div bristol myers squibb
Bristol myers squibb co

Packagers

Baxter International Inc.
Liberty Pharmaceuticals
Prescript Pharmaceuticals
Primedics Laboratories
Sandoz

Dosage forms

Form	Route	Strength
Liquid	Intramuscular; Intravenous	50 mg

Prices

Unit description	Cost	Unit
Chlorpromazine 25 mg/ml amp	8.04USD	ml
Chlorpromazine 200 mg tablet	1.05USD	tablet
Chlorpromazine Hcl 25 mg/ml	0.88USD	ml
Chlorpromazine 100 mg tablet	0.39USD	tablet
Novo-Chlorpromazine 100 mg Tablet	0.35USD	tablet
Chlorpromazine 10 mg tablet	0.32USD	tablet
Chlorpromazine 50 mg tablet	0.3USD	tablet
Novo-Chlorpromazine 50 mg Tablet	0.21USD	tablet
Novo-Chlorpromazine 25 mg Tablet	0.18USD	tablet
Chlorpromazine 25 mg tablet	0.17USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Liquid

Experimental Properties

Property	Value	Source
melting point (°C)	< 25 °C	PhysProp
boiling point (°C)	203-210 °C at 3.00E-01 mm Hg	PhysProp
water solubility	14.2 mg/L (at 24 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	4.55	HANSCH,C ET AL. (1995)
logS	-4.3	ADME Research, USCD
pKa	9.36	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.0207 mg/mL	ALOGPS
logP	4.63	ALOGPS
logP	3.93	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.95 m³·mol^-1	ChemAxon
Polarizability	32.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9718
Blood Brain Barrier	+	0.987
Caco-2 permeable	+	0.8813
P-glycoprotein substrate	Substrate	0.7933
P-glycoprotein inhibitor I	Inhibitor	0.6857
P-glycoprotein inhibitor II	Inhibitor	0.6352
Renal organic cation transporter	Inhibitor	0.7561
CYP450 2C9 substrate	Non-substrate	0.7526
CYP450 2D6 substrate	Substrate	0.9334
CYP450 3A4 substrate	Substrate	0.5578
CYP450 1A2 substrate	Inhibitor	0.8935
CYP450 2C9 inhibitor	Non-inhibitor	0.9483
CYP450 2D6 inhibitor	Inhibitor	0.9622
CYP450 2C19 inhibitor	Non-inhibitor	0.798
CYP450 3A4 inhibitor	Non-inhibitor	0.9166
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6784
Ames test	Non AMES toxic	0.9176
Carcinogenicity	Non-carcinogens	0.9545
Biodegradation	Not ready biodegradable	0.9921
Rat acute toxicity	2.9416 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9662
hERG inhibition (predictor II)	Inhibitor	0.7828

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (9.05 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-0a4r-9230000000-62cbfd979fa705bc6b5e
GC-MS Spectrum - EI-B	GC-MS	splash10-053i-9470000000-c8ea76fcc1b124b82db0
GC-MS Spectrum - CI-B	GC-MS	splash10-000i-2090000000-c38077fbc5880feb7eab
Mass Spectrum (Electron Ionization)	MS	splash10-0a4i-9430000000-708a7cbef8d61ce76846
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as 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: Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Tertiary aliphatic/aromatic amine / Para-thiazine / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Thioether
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: phenothiazines, tertiary amine (CHEBI:8459)

Targets

Details1. D(2) dopamine receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details2. 5-hydroxytryptamine receptor 2A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Virus receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name: HTR2A
Uniprot ID: P28223
Uniprot Name: 5-hydroxytryptamine receptor 2A
Molecular Weight: 52602.58 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Govitrapong P, Chagkutip J, Turakitwanakan W, Srikiatkhachorn A: Platelet 5-HT(2A) receptors in schizophrenic patients with and without neuroleptic treatment. Psychiatry Res. 2000 Sep 25;96(1):41-50. [PubMed:10980325]
Govitrapong P, Mukda S, Turakitwanakan W, Dumrongphol H, Chindaduangratn C, Sanvarinda Y: Platelet serotonin transporter in schizophrenic patients with and without neuroleptic treatment. Neurochem Int. 2002 Oct;41(4):209-16. [PubMed:12106771]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	15.87	N/A	N/A	2904784

Details3. 5-hydroxytryptamine receptor 2C

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name: HTR2C
Uniprot ID: P28335
Uniprot Name: 5-hydroxytryptamine receptor 2C
Molecular Weight: 51820.705 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details4. D(1A) dopamine receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name: DRD1
Uniprot ID: P21728
Uniprot Name: D(1A) dopamine receptor
Molecular Weight: 49292.765 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details5. D(4) dopamine receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Sh3 domain binding
Specific Function: Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name: DRD4
Uniprot ID: P21917
Uniprot Name: D(4) dopamine receptor
Molecular Weight: 48359.86 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details6. Muscarinic acetylcholine receptor M4

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	149.25	N/A	N/A	2904784
Ki (nM)	150	N/A	N/A	6149136

Details7. Muscarinic acetylcholine receptor M2

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details8. Muscarinic acetylcholine receptor M3

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details9. Muscarinic acetylcholine receptor M1

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details10. Alpha-1B adrenergic receptor

Kind: Protein
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...
Gene Name: ADRA1B
Uniprot ID: P35368
Uniprot Name: Alpha-1B adrenergic receptor
Molecular Weight: 56835.375 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Details11. Muscarinic acetylcholine receptor M5

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details12. Alpha-1A adrenergic receptor

Kind: Protein
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...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	2454.71	N/A	N/A	22793499
Ki (nM)	2	N/A	N/A	2904784 / 6149136

Details13. Histamine H1 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Hals PA, Hall H, Dahl SG: Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12. [PubMed:2899826]

Details14. Alpha-1D adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Alpha1-adrenergic receptor activity
Specific Function: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name: ADRA1D
Uniprot ID: P25100
Uniprot Name: Alpha-1D adrenergic receptor
Molecular Weight: 60462.205 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Enzymes

Details1. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Details2. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Curator comments: This enzyme action is supported by limited in vitro studies.

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Wojcikowski J, Boksa J, Daniel WA: Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines. Biochem Pharmacol. 2010 Oct 15;80(8):1252-9. doi: 10.1016/j.bcp.2010.06.045. Epub 2010 Jul 6. [PubMed:20615392]
Daniel WA, Kot M, Wojcikowski J: Influence of classic and atypical neuroleptics on caffeine oxidation in rat liver microsomes. Pol J Pharmacol. 2003 Nov-Dec;55(6):1055-61. [PubMed:14730101]
Wojcikowski J, Pichard-Garcia L, Maurel P, Daniel WA: Contribution of human cytochrome p-450 isoforms to the metabolism of the simplest phenothiazine neuroleptic promazine. Br J Pharmacol. 2003 Apr;138(8):1465-74. doi: 10.1038/sj.bjp.0705195. [PubMed:12721102]

Details3. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-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 performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Details4. Cytochrome P450 2C9

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: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Wojcikowski J, Pichard-Garcia L, Maurel P, Daniel WA: Contribution of human cytochrome p-450 isoforms to the metabolism of the simplest phenothiazine neuroleptic promazine. Br J Pharmacol. 2003 Apr;138(8):1465-74. doi: 10.1038/sj.bjp.0705195. [PubMed:12721102]

Details5. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

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

Wojcikowski J, Pichard-Garcia L, Maurel P, Daniel WA: Contribution of human cytochrome p-450 isoforms to the metabolism of the simplest phenothiazine neuroleptic promazine. Br J Pharmacol. 2003 Apr;138(8):1465-74. doi: 10.1038/sj.bjp.0705195. [PubMed:12721102]

Drug created on June 13, 2005 07:24 / Updated on April 03, 2019 09:35

Promazine

Identification

Structure for Promazine (DB00420)

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Enzymes

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