Drug Information

General Information
Drug ID
DR00268
Drug Name
Norepinephrine
Synonyms
(-)-(R)-Norepinephrine; (-)-Arterenol; (-)-Arterenol free base; (-)-NORADRENALINE; (-)-Norepinephrine; (-)-alpha-(Aminomethyl)protocatechuyl alcohol; (R)-(-)-Norepinephrine; (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol; (R)-Noradrenaline; (R)-Norepinephrine; 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-(9CI); 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol; 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol; ALBB-006229; Adrenor; Aktamin; Arterenol; D-(-)-Noradrenaline; D53D5E3A-2360-4CA9-8031-6C2CD4062FD5; L-1-(3,4-Dihydroxyphenyl)-2-aminoethanol; L-2-Amino-1-(3,4-dihydroxyphenyl)ethanol; L-3,4-dihydroxyphenylethanolamine; L-Noradrenaline; L-Norepinephrine; L-alpha-(aminomethyl)-3,4-dihydroxybenzyl alcohol; L-arterenol; LT03330026; LT4; Levarterenol; Levarterenolo; Levarterenolo [DCIT]; Levoarterenol; Levonor; Levonoradrenaline; Levonorepinephrine; Levophed; Nor adrenalin; Nor adrenalin (TN); Noradrenalin; Noradrenalina; Noradrenalina [Italian]; Noradrenaline; Noradrenaline (JP15); Noradrenalinum; Noreinefrina; Noreinefrina [INN-Spanish]; Norepinefrina; Norepinephrine (INN); Norepinephrine Noradrenalin; Norepinephrine [INN:JAN]; Norepinephrine l-Tartrate (1:1); Norepinephrinum; Norepinephrinum [INN-Latin]; Norepirenamine; Sympathin E
Drug Type
Small molecular drug
Indication Neurogenic shock [ICD11:MG40.Y] Approved [1]
Septic shock [ICD11:1G41] Approved [1]
Therapeutic Class
Vasoconstrictor Agents
Structure
3D MOL 2D MOL
Formula
C8H11NO3
Canonical SMILES
C1=CC(=C(C=C1C(CN)O)O)O
InChI
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChIKey
SFLSHLFXELFNJZ-QMMMGPOBSA-N
CAS Number
CAS 51-41-2
Pharmaceutical Properties Molecular Weight 169.18 Topological Polar Surface Area 86.7
Heavy Atom Count 12 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
XLogP
-1.2
PubChem CID
439260
PubChem SID
10298272 ,11335405 ,11360644 ,11363903 ,11366465 ,11369027 ,11371679 ,11373774 ,11377189 ,11461616 ,11484784 ,11488880 ,11490336 ,11491893 ,11494823 ,15898897 ,22426371 ,24714977 ,24891196 ,26512253 ,26611841 ,26679364 ,26683762 ,26754493 ,26754494 ,29215339 ,36883508 ,3828 ,46394455 ,46506201 ,47291023 ,47662149 ,47959614 ,48034990 ,48259106 ,48416337 ,49892614 ,50109852 ,50109853 ,51036046 ,53788371 ,56311831 ,56313397 ,57288371 ,7847144 ,7980168 ,8144526 ,8149447 ,840952 ,841792
ChEBI ID
ChEBI:18357
TTD Drug ID
D07MOX
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
2-Oct Transporter Info Organic cation transporter 2 Substrate [3]
3-Oct Transporter Info Organic cation transporter 3 Substrate [3]
GLYT2 Transporter Info Sodium- and chloride-dependent glycine transporter 2 Substrate [4]
NET Transporter Info Sodium-dependent noradrenaline transporter Substrate [5]
VMAT1 Transporter Info Vesicular amine transporter 1 Substrate [6]
VMAT2 Transporter Info Vesicular amine transporter 2 Substrate [6]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 2-Oct Transporter Info Km =1500 microM Human embryonic kidney cells (HEK293)-OCT2 [3]
2-Oct Transporter Info Km =1900 microM Oocytes-OCT2 [7]
3-Oct Transporter Info Km =510 microM Human embryonic kidney cells (HEK293)-OCT3 [8]
3-Oct Transporter Info Km =2630 microM Human embryonic kidney cells (HEK293)-OCT3 [3]
NET Transporter Info Km =690 microM Monkey kidney fibroblast-like cell (COS)1-NET [9]
References
1 Norepinephrine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
3 Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
4 SLC6A2 Gene (Protein Coding).
5 Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51.
6 SLC18: Vesicular neurotransmitter transporters for monoamines and acetylcholine. Mol Aspects Med. 2013 Apr-Jun;34(2-3):360-72.
7 Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52.
8 Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51.
9 chi-Conotoxin and tricyclic antidepressant interactions at the norepinephrine transporter define a new transporter model. J Biol Chem. 2007 Jun 15;282(24):17837-44.

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