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norepinephrine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
sympathomimetic, phenethyl derivatives	1960	51-41-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: norepinephrine (R)-Norepinephrine arterenol levarterenol noradrenaline norepinephrine bitartrate (-)-noradrenaline	Precursor of epinephrine that is secreted by the ADRENAL MEDULLA and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers, and of the diffuse projection system in the brain that arises from the LOCUS CERULEUS. It is also found in plants and is used pharmacologically as a sympathomimetic. Molecular weight: 169.18 Formula: C8H11NO3 CLOGP: -0.99 LIPINSKI: 0 HAC: 4 HDO: 4 TPSA: 86.71 ALOGS: -1.13 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

norepinephrine
(R)-Norepinephrine
arterenol
levarterenol
noradrenaline
norepinephrine bitartrate
(-)-noradrenaline

Precursor of epinephrine that is secreted by the ADRENAL MEDULLA and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers, and of the diffuse projection system in the brain that arises from the LOCUS CERULEUS. It is also found in plants and is used pharmacologically as a sympathomimetic.

Molecular weight: 169.18
Formula: C8H11NO3
CLOGP: -0.99
LIPINSKI: 0
HAC: 4
HDO: 4
TPSA: 86.71
ALOGS: -1.13
ROTB: 2

Status: OFP

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

Drug dosage:

Dose	Unit	Route
6	mg	P

ADMET properties:

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Property	Value	Reference
S (Water solubility)	849 mg/mL	Bocci G, Oprea TI, Benet LZ
BA (Bioavailability)	3 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
July 13, 1950	FDA	HOSPIRA

FDA Adverse Event Reporting System (Female)

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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
Multiple organ dysfunction syndrome	414.66	27.21	226	15687	56526	63416583
Drug ineffective	321.85	27.21	762	15151	1044003	62429106
Cardiac arrest	301.61	27.21	221	15692	92324	63380785
Septic shock	299.47	27.21	194	15719	66435	63406674
Metabolic acidosis	273.45	27.21	159	15754	44910	63428199
Shock	245.17	27.21	119	15794	23344	63449765
Myoglobin urine present	239.15	27.21	52	15861	720	63472389
Hypotension	204.97	27.21	294	15619	272310	63200799
Stress cardiomyopathy	197.11	27.21	78	15835	9372	63463737
Intentional overdose	195.07	27.21	156	15757	73996	63399113

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FDA Adverse Event Reporting System (Male)

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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
Multiple organ dysfunction syndrome	609.23	21.16	427	18745	76139	34861620
Drug ineffective	531.32	21.16	914	18258	455837	34481922
Cardiogenic shock	450.68	21.16	241	18931	26377	34911382
Appendicolith	370.72	21.16	149	19023	8452	34929307
Appendicitis	299.00	21.16	151	19021	14656	34923103
Ventricular fibrillation	229.80	21.16	148	19024	22806	34914953
Septic shock	205.59	21.16	224	18948	71610	34866149
Sepsis	190.60	21.16	333	18839	166228	34771531
Ascites	170.76	21.16	166	19006	46405	34891354
Off label use	163.00	21.16	551	18621	418973	34518786

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FDA Adverse Event Reporting System (Geriatric)

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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
Multiple organ dysfunction syndrome	961.77	20.13	609	32925	119637	79591217
Drug ineffective	907.63	20.13	1615	31919	1079298	78631556
Cardiogenic shock	626.66	20.13	320	33214	41594	79669260
Septic shock	455.95	20.13	392	33142	122409	79588445
Appendicolith	406.09	20.13	148	33386	8403	79702451
Cardiac arrest	405.18	20.13	427	33107	171669	79539185
Shock	338.39	20.13	217	33317	43331	79667523
Metabolic acidosis	327.71	20.13	274	33260	82255	79628599
Hypotension	316.05	20.13	619	32915	439698	79271156
Ventricular fibrillation	314.16	20.13	185	33349	31741	79679113

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FDA Adverse Event Reporting System (Pediatric)

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Pharmacologic Action:

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Source	Code	Description
ATC	C01CA03	CARDIOVASCULAR SYSTEM CARDIAC THERAPY CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES Adrenergic and dopaminergic agents
CHEBI has role	CHEBI:25512	neurotransmitters
CHEBI has role	CHEBI:35524	sympathomimetic
CHEBI has role	CHEBI:35569	alpha-adrenergic agonists
CHEBI has role	CHEBI:75771	Mus musculus metabolites
CHEBI has role	CHEBI:76967	human xenobiotic metabolites
FDA CS	M0003647	Catecholamines
FDA EPC	N0000175570	Catecholamine
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D000322	Adrenergic Agonists

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Bronchiectasis	indication	12295008	DOID:9563
Bronchitis	indication	32398004	DOID:6132
Low blood pressure	indication	45007003
Pulmonary emphysema	indication	87433001
Asthma	indication	195967001	DOID:2841
Asthma management	indication	406162001
Acute exacerbation of asthma	indication	708038006
Hypovolemia	contraindication	28560003
Hypercapnia	contraindication	29596007
Hypertensive disorder	contraindication	38341003	DOID:10763

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🐶 Veterinary Drug Use

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🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.41	acidic
pKa2	12.03	acidic
pKa3	12.63	acidic
pKa4	8.83	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
EQ 16MG BASE/250ML (EQ 64MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	10226436	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 16MG BASE/250ML (EQ 64MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	10420735	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 16MG BASE/250ML (EQ 64MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	11413259	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 4MG BASE/250 ML (EQ 16MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	10226436	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 4MG BASE/250 ML (EQ 16MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	10420735	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 4MG BASE/250 ML (EQ 16MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	11413259	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 8MG BASE/250ML (EQ 32MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	10226436	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 8MG BASE/250ML (EQ 32MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	10420735	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION
EQ 8MG BASE/250ML (EQ 32MCG BASE/ML)	NOREPINEPHRINE BITARTRATE IN 0.9% SODIUM CHLORIDE	LONG GROVE PHARMS	N214628	Oct. 6, 2022	DISCN	SOLUTION	INTRAVENOUS	11413259	Jan. 30, 2038	INDICATED TO RAISE BLOOD PRESSURE IN ADULT PATIENTS WITH SEVERE, ACUTE HYPOTENSION

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Orange Book exclusivity data (new drug applications)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN	AGONIST	Ki	7.20	CHEMBL	CHEMBL
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN	AGONIST	Ki	5.82	CHEMBL	CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	AGONIST	Ki	7.40	IUPHAR	CHEMBL
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN	AGONIST	Ki	4.69	CHEMBL	CHEMBL
Beta-2 adrenergic receptor	GPCR	P07550	ADRB2_HUMAN	AGONIST	Kd	5.40	CHEMBL	CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN	AGONIST	Ki	7.18	CHEMBL	CHEMBL
Beta-1 adrenergic receptor	GPCR	P08588	ADRB1_HUMAN	AGONIST	Ki	6	IUPHAR	CHEMBL
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN		Kd	4.30	CHEMBL
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	5.89	CHEMBL
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	6.48	PDSP

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External reference:

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ID	Source
LT4	PDB_CHEM_ID
001777	NDDF
004718	NDDF
108341-18-0	SECONDARY_CAS_RN
111130009	SNOMEDCT_US
2706	MMSL
33	INN_ID
333906	MMSL
35060	MMSL
4018242	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Levophed	HUMAN PRESCRIPTION DRUG LABEL	1	0409-1443	INJECTION, SOLUTION, CONCENTRATE	1 mg	INTRAVENOUS	NDA	20 sections
Levophed	HUMAN PRESCRIPTION DRUG LABEL	1	0409-1443	INJECTION, SOLUTION, CONCENTRATE	1 mg	INTRAVENOUS	NDA	20 sections
LEVOPHED	Human prescription drug label	1	0409-3375	INJECTION, SOLUTION, CONCENTRATE	1 mg	INTRAVENOUS	NDA	27 sections
LEVOPHED	Human prescription drug label	1	0409-3375	INJECTION, SOLUTION, CONCENTRATE	1 mg	INTRAVENOUS	NDA	27 sections
Norepinephrine Bitartrate	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9318	INJECTION	1 mg	INTRAVENOUS	ANDA	24 sections
NOREPINEPHRINE BITARTRATE	HUMAN PRESCRIPTION DRUG LABEL	1	0338-0108	INJECTION, SOLUTION	8 mg	INTRAVENOUS	NDA	24 sections
NOREPINEPHRINE BITARTRATE	HUMAN PRESCRIPTION DRUG LABEL	1	0338-0108	INJECTION, SOLUTION	8 mg	INTRAVENOUS	NDA	24 sections
NOREPINEPHRINE BITARTRATE	HUMAN PRESCRIPTION DRUG LABEL	1	0338-0108	INJECTION, SOLUTION	8 mg	INTRAVENOUS	NDA	24 sections
NOREPINEPHRINE BITARTRATE	HUMAN PRESCRIPTION DRUG LABEL	1	0338-0108	INJECTION, SOLUTION	8 mg	INTRAVENOUS	NDA	24 sections
NOREPINEPHRINE BITARTRATE	HUMAN PRESCRIPTION DRUG LABEL	1	0338-0112	INJECTION, SOLUTION	4 mg	INTRAVENOUS	NDA	24 sections

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