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

Stem definition	Drug id	CAS RN
atropine derivatives	1475	60205-81-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ipratropium ipratropium bromide ipratropium bromide hydrate ipratropium bromide monohydrate	A muscarinic antagonist structurally related to ATROPINE but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic. Molecular weight: 332.46 Formula: C20H30NO3 CLOGP: -2.19 LIPINSKI: 0 HAC: 4 HDO: 1 TPSA: 46.53 ALOGS: -5.48 ROTB: 6 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ipratropium
ipratropium bromide
ipratropium bromide hydrate
ipratropium bromide monohydrate

A muscarinic antagonist structurally related to ATROPINE but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic.

Molecular weight: 332.46
Formula: C20H30NO3
CLOGP: -2.19
LIPINSKI: 0
HAC: 4
HDO: 1
TPSA: 46.53
ALOGS: -5.48
ROTB: 6

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.24	mg	N
0.12	mg	Inhal.aerosol
0.12	mg	Inhal.powder
0.30	mg	Inhal.solution

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.01 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	3 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	5.10 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	31.40 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.95 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.64 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 29, 1986	FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Asthma	536.68	34.90	122	777	11192	2345994
Dyspnoea	364.31	34.90	139	760	78594	2278592
Wheezing	253.54	34.90	60	839	6324	2350862
Obstructive airways disorder	232.88	34.90	43	856	1330	2355856
Pneumonia	172.72	34.90	72	827	49224	2307962
Chronic obstructive pulmonary disease	157.86	34.90	42	857	7035	2350151
Drug ineffective	142.28	34.90	79	820	101545	2255641
Cough	138.27	34.90	55	844	33062	2324124
Blood count abnormal	125.24	34.90	28	871	2254	2354932
Lactic acidosis	106.29	34.90	29	870	5301	2351885
Lung hyperinflation	101.25	34.90	15	884	109	2357077
Infective exacerbation of chronic obstructive airways disease	96.17	34.90	15	884	159	2357027
PCO2 increased	95.17	34.90	15	884	171	2357015
Hyperkalaemia	94.34	34.90	27	872	5866	2351320
Blood pH decreased	93.52	34.90	17	882	474	2356712
Blood lactic acid increased	90.18	34.90	18	881	833	2356353
Off label use	88.30	34.90	52	847	73546	2283640
PO2 decreased	87.04	34.90	15	884	305	2356881
Influenza B virus test positive	85.71	34.90	11	888	21	2357165
Oxygen saturation decreased	83.38	34.90	26	873	7560	2349626
Airway peak pressure increased	82.46	34.90	11	888	32	2357154
Blood bicarbonate decreased	80.27	34.90	15	884	488	2356698
Productive cough	78.99	34.90	23	876	5298	2351888
Dyspnoea exertional	77.35	34.90	23	876	5697	2351489
Bronchospasm	77.08	34.90	20	879	3004	2354182
Therapeutic product effect incomplete	75.00	34.90	26	873	10505	2346681
Respiratory rate increased	74.36	34.90	17	882	1503	2355683
Respiratory acidosis	72.93	34.90	15	884	806	2356380
Hypercapnia	72.64	34.90	14	885	538	2356648
Condition aggravated	67.48	34.90	33	866	31946	2325240
Tachycardia	67.23	34.90	27	872	16382	2340804
Acute kidney injury	62.25	34.90	30	869	28092	2329094
Cyanosis	61.87	34.90	17	882	3168	2354018
Tremor	61.22	34.90	27	872	20634	2336552
Status asthmaticus	60.81	34.90	10	889	151	2357035
Seizure	59.94	34.90	28	871	24438	2332748
Atrial fibrillation	57.56	34.90	23	876	13745	2343441
Muscular weakness	55.80	34.90	23	876	14874	2342312
Drug hypersensitivity	53.15	34.90	32	867	46611	2310575
Chest discomfort	52.85	34.90	22	877	14573	2342613
Hypertension	51.04	34.90	26	873	27335	2329851
Neutropenia	50.71	34.90	24	875	21524	2335662
Type 2 diabetes mellitus	48.63	34.90	13	886	2181	2355005
Nausea	45.10	34.90	41	858	112148	2245038
Product quality issue	44.91	34.90	18	881	10811	2346375
Blood test abnormal	44.88	34.90	11	888	1307	2355879
Acute respiratory failure	44.44	34.90	13	886	3025	2354161
Pruritus	42.38	34.90	27	872	43313	2313873
Pupils unequal	42.10	34.90	8	891	284	2356902
Angle closure glaucoma	40.03	34.90	9	890	735	2356451
Hyper IgE syndrome	39.50	34.90	5	894	8	2357178
Tachypnoea	39.15	34.90	11	888	2218	2354968
Lymphocyte count decreased	38.87	34.90	12	887	3351	2353835
Neutrophil count decreased	38.29	34.90	14	885	6553	2350633
Urinary retention	37.85	34.90	12	887	3655	2353531
Respiratory failure	37.82	34.90	17	882	13511	2343675
Drug reaction with eosinophilia and systemic symptoms	36.81	34.90	13	886	5505	2351681
Emphysema	36.65	34.90	9	890	1076	2356110
Cardiac arrest	36.22	34.90	17	882	14913	2342273
Erythema	35.84	34.90	20	879	25139	2332047
Leukopenia	35.63	34.90	15	884	10181	2347005
Pancoast's syndrome	35.42	34.90	4	895	0	2357186
Toxic epidermal necrolysis	35.41	34.90	11	888	3133	2354053

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Dyspnoea	279.89	37.50	112	637	51947	1694085
Asthma	271.57	37.50	64	685	4840	1741192
Chronic obstructive pulmonary disease	209.24	37.50	54	695	5899	1740133
Wheezing	113.64	37.50	31	718	4122	1741910
Drug ineffective	105.89	37.50	62	687	63739	1682293
Pupils unequal	100.55	37.50	17	732	219	1745813
Oxygen saturation decreased	82.69	37.50	26	723	5649	1740383
Obstructive airways disorder	80.29	37.50	18	731	1056	1744976
Blood count abnormal	74.83	37.50	18	731	1439	1744593
Cough	70.39	37.50	32	717	19165	1726867
Tachypnoea	66.23	37.50	18	731	2340	1743692
Therapeutic product effect incomplete	63.15	37.50	21	728	5427	1740605
Condition aggravated	61.33	37.50	30	719	21120	1724912
Pneumonia	58.52	37.50	38	711	46144	1699888
Productive cough	54.51	37.50	17	732	3574	1742458
Sputum discoloured	54.15	37.50	12	737	665	1745367
Chest discomfort	53.37	37.50	20	729	7311	1738721
Tachycardia	52.42	37.50	23	726	12605	1733427
Off label use	46.95	37.50	31	718	38540	1707492
Hyperkaliuria	46.14	37.50	6	743	8	1746024
Bronchiectasis	45.13	37.50	10	739	553	1745479
Tachycardia foetal	44.73	37.50	7	742	53	1745979
Oedema peripheral	41.84	37.50	21	728	15529	1730503
Arrhythmia	38.66	37.50	15	734	6001	1740031
Medication error	38.38	37.50	14	735	4729	1741303
Thrombocytopenia	38.34	37.50	22	727	21227	1724805
Confusional state	38.32	37.50	22	727	21256	1724776
Cholestasis	37.96	37.50	13	736	3652	1742380

Pharmacologic Action:

Source	Code	Description
ATC	R01AX03	RESPIRATORY SYSTEM NASAL PREPARATIONS DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE Other nasal preparations
ATC	R03AL01	RESPIRATORY SYSTEM DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES ADRENERGICS, INHALANTS Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
ATC	R03AL02	RESPIRATORY SYSTEM DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES ADRENERGICS, INHALANTS Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
ATC	R03BB01	RESPIRATORY SYSTEM DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS Anticholinergics
FDA EPC	N0000175574	Anticholinergic
MeSH PA	D018927	Anti-Asthmatic Agents
MeSH PA	D001993	Bronchodilator Agents
MeSH PA	D018678	Cholinergic Agents
MeSH PA	D018680	Cholinergic Antagonists
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D019141	Respiratory System Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Bronchospasm	indication	4386001
Chronic obstructive lung disease	indication	13645005	DOID:3083
Bronchitis	indication	32398004	DOID:6132
Allergic rhinitis	indication	61582004
Nasal discharge	indication	64531003
Pulmonary emphysema	indication	87433001
Chronic Obstructive Pulmonary Disease with Bronchospasms	indication
Asthma	off-label use	195967001	DOID:2841
Asthma-chronic obstructive pulmonary disease overlap syndrome	off-label use	10692761000119107
Ocular hypertension	contraindication	4210003	DOID:9282
Hyperthyroidism	contraindication	34486009	DOID:7998
Hypertensive disorder	contraindication	38341003	DOID:10763
Hypokalemia	contraindication	43339004
Conduction disorder of the heart	contraindication	44808001
Ketoacidosis	contraindication	56051008
Metabolic acidosis	contraindication	59455009
Diabetes mellitus	contraindication	73211009	DOID:9351
Paradoxical bronchospasm	contraindication	102578005
Prolonged QT interval	contraindication	111975006
Seizure disorder	contraindication	128613002
Bladder outflow obstruction	contraindication	236645006
Benign prostatic hyperplasia	contraindication	266569009
Retention of urine	contraindication	267064002
Angle-closure glaucoma	contraindication	392291006	DOID:13550
Chronic myocardial ischemia	contraindication	413844008	DOID:3393
Myocardial ischemia	contraindication	414795007	DOID:3393
Congenital long QT syndrome	contraindication	442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.24	acidic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.017% Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons	DUONEB	MYLAN SPECIALITY LP	N020950	March 21, 2001	DISCN	SOLUTION	INHALATION	6632842	Dec. 28, 2021	TREATMENT OF BRONCHOSPASM ASSOCIATED WITH COPD IN PATIENTS REQUIRING MORE THAN ONE BRONCHO DILATOR

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Muscarinic acetylcholine receptor M3	GPCR	P20309	ACM3_HUMAN	ANTAGONIST	Ki	9.29	WOMBAT-PK	CHEMBL
Solute carrier family 22 member 2	Transporter	O15244	S22A2_HUMAN		IC50	4.82	WOMBAT-PK
Muscarinic acetylcholine receptor M5	GPCR	P08912	ACM5_HUMAN		Ki	8.77	WOMBAT-PK
Muscarinic acetylcholine receptor M4	GPCR	P08173	ACM4_HUMAN		Ki	9.18	WOMBAT-PK
Muscarinic acetylcholine receptor M2	GPCR	P08172	ACM2_HUMAN		Ki	8.82	WOMBAT-PK
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	9.31	WOMBAT-PK
Muscarinic acetylcholine receptor M1	GPCR		ACM1_RAT		Ki	9.54	CHEMBL
Muscarinic acetylcholine receptor M3	GPCR		ACM3_RAT		Ki	9.74	CHEMBL
Muscarinic acetylcholine receptor M2	GPCR		ACM2_RAT		Ki	9.11	CHEMBL

External reference:

ID	Source
4019791	VUID
N0000147880	NUI
C0027235	UMLSCUI
D02212	KEGG_DRUG
108624006	SNOMEDCT_US
4019791	VANDF
7213	RXNORM
372518007	SNOMEDCT_US
d00265	MMSL
004943	NDDF
DB00332	DRUGBANK_ID
J697UZ2A9J	UNII
66985-17-9	SECONDARY_CAS_RN
X8M	PDB_CHEM_ID
CHEBI:5956	CHEBI
657309	PUBCHEM_CID
CHEMBL1464005	ChEMBL_ID
D009241	MESH_DESCRIPTOR_UI
CHEMBL1621597	ChEMBL_ID
CHEMBL2134724	ChEMBL_ID
325	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	0781-7157	SOLUTION	0.50 mg	RESPIRATORY (INHALATION)	ANDA	13 sections
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	21695-911	SOLUTION	0.50 mg	RESPIRATORY (INHALATION)	ANDA	13 sections
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	42254-041	SOLUTION	0.50 mg	RESPIRATORY (INHALATION)	ANDA	12 sections
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	42254-355	SPRAY, METERED	42 ug	NASAL	ANDA	13 sections
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	54868-4082	SOLUTION	0.50 mg	RESPIRATORY (INHALATION)	ANDA	13 sections
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5049	SPRAY, METERED	42 ug	NASAL	ANDA	13 sections
AtroventHFA	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5511	AEROSOL, METERED	17 ug	RESPIRATORY (INHALATION)	NDA	14 sections
Atrovent	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5565	SPRAY, METERED	21 ug	NASAL	NDA	14 sections
Ipratropium Bromide	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5751	SPRAY, METERED	21 ug	NASAL	ANDA	12 sections
Ipratropium Bromide and Albuterol Sulfate	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5974	SOLUTION	0.50 mg	RESPIRATORY (INHALATION)	NDA	12 sections