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Levobetaxolol

HCID 60657
NotesReactions
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
93221-48-8
Standard SMILES
CC(C)NC[C@H](O)COc1ccc(CCOCC2CC2)cc1
InChIKey
NWIUTZDMDHAVTP-KRWDZBQOSA-N
Molecular formula
C18H29NO3
Average molar mass
307.4 g/mol
Monoisotopic mass
307.21474379

Overview

(S)-betaxolol is the (S)-enantiomer of betaxolol. It is an enantiomer of a (R)-betaxolol.

Names & identifiers

Preferred name
Levobetaxolol
IUPAC
(2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol
English name
LEVOBETAXOLOL
Molecular formula
C18H29NO3
Molecular weight
307.43

Names & synonyms

Levobetaxolol(S)-Betaxolol(-)-Betaxolol93221-48-8(S)-(-)-BetaxololBetaxolol, (s)-levobetaxololum(2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol75O9XHA4TUCHEBI:59254DTXSID30239341(2S)-1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-(propan-2-ylamino)propan-2-ol
Show more names
Levoβxolol HCl(2S)-1-[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]-3-(isopropylamino)-2-propanol(2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(isopropylamino)propan-2-ol[S,(-)]-1-[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]-3-(isopropylamino)-2-propanol(S)-1-[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanol
(2S)-1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-(propan-2-ylamino)propan-2-olRefChem:153195DTXCID50161832Levobetaxolol [INN](S)-1-(isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol(2S)-1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-[(propan-2-yl)amino]propan-2-ol(S)-Betaxolol hydrochloride;AL-1577AUNII-75O9XHA4TU

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
50.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
11
Heavy atoms
22
Formal charge
0
Complexity
286

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antihypertensives

Pharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point
71 · 71-72℃
Boiling point
448 · 448.0±40.0 °C(Predicted)
Density
1.067 · 1.067
pka
13.89 · 13.89±0.20(Predicted)
FDA UNII
75 O9XHA4TU · 75O9XHA4TU

Chemistry & industry

Pharmacology

PharmacodynamicsLevobetaxolol is a selective β1 adrenergic receptor antagonist. It acts to lower intraocular pressure. Levobataxolol is condsidered to be the more active component of the betaxolol racemate.
Mechanism of Action · 1 item

The exact mechanism by which levobetaxolol lowers intraocular pressure is not known. It it thought that antagonism of β-adrenergic receptors may reduce the production of aqueous humour stimulated via the cyclic adenosine monophosphate-protein kinase A pathway. It is also thought that the vasoconstriction produced by antagonism of β adrenergic receptors reduces blood flow to the eye and therefore the ultrafiltration responsible for aqueous humour production. β1 selective antagonists are less effective than non-selective β adrenergic receptor antagonists because β2 receptors make up the bulk of the population in the eye. They do, however, come with the benefit of reduced respiratory complications.

Biological Half-LifeThe mean half life of levobetaxolol is 20 h.
Absorption, Distribution and ExcretionLevobetaxolol is applied topically to the eye but some does reach systemic circulaton with a Tmax of 3 h.

Applications

UsesAnti-adrenergic (β-receptor).

Suppliers15 total

Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
上海陶术生物科技股份有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
93221-48-8
PubChem CID
60657
DTXSID
DTXSID30239341
ChEMBL
CHEMBL1201274
ChEBI
CHEBI:59254
UNII
75O9XHA4TU
Nikkaji
J387.170C
+1-781-999-5354; +1-00000000000 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
南京罗迈美生物科技有限公司[email protected]
武汉研哲科技有限公司15527250409 · [email protected]
武汉峰耀同辉化学制品有限公司027-87466105 15377573527 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
陕西衡瀚新材料有限公司15719109892 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海亿万化工有限公司00-18662433356 18662433356 · [email protected]
重庆卡兰医药有限公司[email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]

Additional notes

DefinitionChEBI: (S)-betaxolol is the (S)-enantiomer of betaxolol. It is an enantiomer of a (R)-betaxolol.