Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H25N3O |
Molecular Weight | 347.4534 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C(NC1CCN(CCC2=CNC3=C2C=CC=C3)CC1)C4=CC=CC=C4
InChI
InChIKey=JXZZEXZZKAWDSP-UHFFFAOYSA-N
InChI=1S/C22H25N3O/c26-22(17-6-2-1-3-7-17)24-19-11-14-25(15-12-19)13-10-18-16-23-21-9-5-4-8-20(18)21/h1-9,16,19,23H,10-15H2,(H,24,26)
Molecular Formula | C22H25N3O |
Molecular Weight | 347.4534 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB08950
Sources: https://www.drugbank.ca/drugs/DB08950
Indoramin is an alpha-1 selective antagonist of adrenergic receptor, sold under trade names Baratol and Doralese, and now available as a generic. It has no reflex tachycardia and direct myocardial depression action and is used to treat benign prostate hyperplasia (as 20 mg tablets) or reduce blood pressure (as 25 mg strength tablets). It was also investigated as a treatment of a migraine and congestive heart failure.
CNS Activity
Originator
Sources: https://www.google.com/patents/US3527761
Curator's Comment: # Wyeth John & Brother Ltd
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028 |
8.4 null [pKi] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028 |
7.4 null [pKi] | ||
Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028 |
6.8 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | DORALESE Approved UseIndoramin 20 mg Tablets are used for a condition called ‘benign prostatic hyperplasia’ or BPH. The prostate is a gland found underneath the bladder in men. It surrounds the tube (called the urethra) which carries urine from the bladder to the outside of the body. |
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Primary | BARATOL Approved UseBaratol Tablets are used to reduce high blood pressure. |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/49624 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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A double-blind comparison of indoramin and propranolol in the treatment of moderate to severe essential hypertension. | 1983 |
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Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin. | 1986 Feb |
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The alpha 1-adrenergic receptor that mediates smooth muscle contraction in human prostate has the pharmacological properties of the cloned human alpha 1c subtype. | 1994 Apr |
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Use of recombinant alpha 1-adrenoceptors to characterize subtype selectivity of drugs for the treatment of prostatic hypertrophy. | 1995 Jan 16 |
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Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification. | 1997 Jul |
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Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies. | 1999 Apr 16 |
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A double-blind randomized placebo-controlled trial of oral indoramin to treat chronic anal fissure. | 2001 May |
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[Migraine: a disease, not a symptom]. | 2002 Jan 1 |
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Prokinetic effect of indoramin, an alpha-adrenergic antagonist, on human gall-bladder. | 2002 Oct |
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The medical and surgical management of chronic anal fissure. | 2002 Sep |
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Use of alpha-blockers and the risk of hip/femur fractures. | 2003 Dec |
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Drug-related hyperprolactinemia. | 2003 Feb |
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Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens. | 2003 Jul |
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[Drug-induced hyperprolactinemia: a case-non-case study from the national pharmacovigilance database]. | 2003 Mar-Apr |
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Effect of cyproterone acetate on alpha1-adrenoceptor subtypes in rat vas deferens. | 2003 Nov |
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Current treatment options for fissure-in-ano. | 2004 Jan-Mar |
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5-Alpha reductase inhibition provides superior benefits to alpha blockade by preventing AUR and BPH-related surgery. | 2004 May |
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Khat chewing and arterial blood pressure. A randomized controlled clinical trial of alpha-1 and selective beta-1 adrenoceptor blockade. | 2005 Apr |
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Pharmacological advancements in the treatment of chronic anal fissure. | 2005 Nov |
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Increased cholinergic contractions of jejunal smooth muscle caused by a high cholesterol diet are prevented by the 5-HT4 agonist--tegaserod. | 2006 Feb 23 |
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Non surgical therapy for anal fissure. | 2006 Oct 18 |
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Multiple GPCR conformations and signalling pathways: implications for antagonist affinity estimates. | 2007 Aug |
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Prokinetic effect of alpha-adrenergic antagonist, and beta-adrenergic antagonist on gall-bladder motility in humans with gall-stone disease. | 2007 Jul |
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Pharmacological causes of hyperprolactinemia. | 2007 Oct |
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Alpha antagonists and intraoperative floppy iris syndrome: A spectrum. | 2008 Dec |
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Recent advances in the pharmacotherapy of chronic anal fissure: an update. | 2008 Jul |
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Optimizing prophylactic treatment of migraine: Subtypes and patient matching. | 2008 Oct |
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Torsade de pointes: a severe and unknown adverse effect in indoramin self-poisoning. | 2009 Apr 3 |
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[Acute bilateral angle-closure glaucoma induced by topiramate: contribution of Visante OCT]. | 2010 May |
Patents
Sample Use Guides
The recommended dose is one tablet (20 mg) twice a day. The tablet should be swallowed with water. Some elderly patients may need just one tablet at night. The patient’s doctor may increase their dose to a maximum total daily dose of 100 mg. The patient must not take more than their doctor has recommended.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6133954
Binding of indoramin to alpha1 receptors was studied using rat cerebral cortex membranes with [3H]prazosin to label alpha1 adrenoreceptors. Indoramin displaces prozasin with IC50 pKi of 7.61.
Substance Class |
Chemical
Created
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Record UNII |
0Z802HMY7H
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C29713
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C02CA02
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m6280
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248-041-5
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CHEMBL279516
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INDORAMIN
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D007217
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26844-12-2
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DB08950
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
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ACTIVE MOIETY |