| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-06-23 18:08:03 |
| Primary Accession Number |
DB00629 |
| Secondary Accession Number |
|
| Name |
Guanabenz |
| Drug Type |
|
| Description |
An alpha-2 selective adrenergic agonist used as an antihypertensive agent. [PubChem] |
| Synonyms |
Not Available |
| Brand Names |
- GBZ
- Guanabenz Acetate
- Guanabenz [USAN:INN]
- Guanabenz(USAN)
- Guanabenzo [INN-Spanish]
- Guanabenzum [INN-Latin]
- Wy 8678 base
- Wytensin
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
2-[(2,6-dichlorophenyl)methylideneamino]guanidine |
| Chemical Formula |
C8H8Cl2N4 |
| Chemical Structure |
 |
| CAS Registry Number |
5051-62-7 |
| InChI Identifier |
InChI=1/C8H8Cl2N4/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12/h1-4H,(H4,11,12,14)/f/h11-12H2 |
| InChI Key |
WDZVGELJXXEGPV-LLDOCCBOCE |
| KEGG Drug |
D04375  |
| KEGG Compound |
C07034  |
| PubChem Compound |
3517  |
| PubChem Substance |
9246  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA449819  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
Not Available |
| PDRhealth Link |
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/gua1612.shtml  |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Guanabenz  |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
Not Available |
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
231.0820 |
| Monoisotopic Molecular Weight |
230.0126 |
| State |
Solid |
| Melting Point |
228 oC |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
8.89e-02 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
3.2
Source: PhysProp
|
| Predicted LogP |
2.25
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-3.41
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
-4.5 [ADME Research, USCD] |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
N\C(N)=N/N=C/C1=C(Cl)C=CC=C1Cl |
| Canonical SMILES |
NC(N)=NN=CC1=C(Cl)C=CC=C1Cl |
| Drug Category |
- Adrenergic alpha-Agonists
- Antihypertensive Agents
- Sympatholytics
|
| ATC Codes |
Not Available |
| AHFS Codes |
Not Available |
| Indication |
For management of High blood pressure |
| Pharmacology |
Guanabenz, a centrally acting α-2 adrenergic agonist, is indicated for treatment of hypertension. |
| Mechanism of Action |
Guanabenz's antihypertensive effect is thought to be due to central alpha-adrenergic stimulation, which results in a decreased sympathetic outflow to the heart, kidneys, and peripheral vasculature in addition to a decreased systolic and diastolic blood pressure and a slight slowing of pulse rate. Chronic administration of guanabenz also causes a decrease in peripheral vascular resistance. |
| Absorption |
Approximately 75% absorbed from gastrointestinal tract |
| Toxicity |
Excessive contraction of the pupils, irritabilitylow blood pressure, sleepiness, slow heartbeat, sluggishness |
| Protein Binding |
90% |
| Biotransformation |
Hepatic |
| Half Life |
6 hours. |
| Dosage Forms |
Not Available
|
| Patient Information |
Not Available |
| Contraindications |
Not Available |
| Interactions |
Not Available |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| General References |
- Drugs.com

- Wikipedia

- PDRhealth

|
| Organisms Affected |
|
| Targets |
- Alpha-2A adrenergic receptor
|
|
Drug Target 1
[top]
|
| Target 1 ID |
318 |
| Target 1 Name |
Alpha-2A adrenergic receptor |
| Target 1 Synonyms |
- Alpha-2 adrenergic receptor subtype C10
- Alpha-2A adrenoceptor
- Alpha-2A adrenoreceptor
- Alpha-2AAR
|
| Target 1 Gene Name |
ADRA2A |
| Target 1 Protein Sequence |
>Alpha-2A adrenergic receptor
MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFGNVLVIIAVFT
SRALKAPQNLFLVSLASADILVATLVIPFSLANEVMGYWYFGKAWCEIYLALDVLFCTSS
IVHLCAISLDRYWSITQAIEYNLKRTPRRIKAIIITVWVISAVISFPPLISIEKKGGGGG
PQPAEPRCEINDQKWYVISSCIGSFFAPCLIMILVYVRIYQIAKRRTRVPPSRRGPDAVA
APPGGTERRPNGLGPERSAGPGGAEAEPLPTQLNGAPGEPAPAGPRDTDALDLEESSSSD
HAERPPGPRRPERGPRGKGKARASQVKPGDSLPRRGPGATGIGTPAAGPGEERVGAAKAS
RWRGRQNREKRFTFVLAVVIGVFVVCWFPFFFTYTLTAVGCSVPRTLFKFFFWFGYCNSS
LNPVIYTIFNHDFRRAFKKILCRGDRKRIV
|
| Target 1 Number of Residues |
457 |
| Target 1 Molecular Weight |
48957 |
| Target 1 Theoretical pI |
10.20 |
| Target 1 GO Classification |
|
Function
|
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
amine receptor activity
adrenoceptor activity
alpha-adrenergic receptor activity
alpha2-adrenergic receptor activity |
|
Process
|
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway |
|
Component
|
cell
membrane
intrinsic to membrane
integral to membrane |
|
| Target 1 General Function |
Involved in alpha2-adrenergic receptor activity |
| Target 1 Specific Function |
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol |
| Target 1 Pathways |
Not Available
|
| Target 1 Reactions |
Not Available |
| Target 1 Pfam Domain Function |
|
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 34-59
- 71-96
- 107-129
- 150-173
- 193-217
- 375-399
- 407-430
|
| Target 1 Essentiality |
Non-Essential |
| Target 1 GenBank ID Protein |
178196  |
| Target 1 UniProtKB/Swiss-Prot ID |
P08913  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
ADA2A_HUMAN  |
| Target 1 PDB ID |
1HOF  |
| Target 1 PDB File |
Show |
| Target 1 3D Structure |
|
| Target 1 Cellular Location |
- Membrane
- multi-pass membrane protein
|
| Target 1 Gene Sequence |
>1353 bp
ATGGGCTCCCTGCAGCCGGACGCGGGCAACGCGAGCTGGAACGGGACCGAGGCGCCGGGG
GGCGGCGCCCGGGCCACCCCTTACTCCCTGCAGGTGACGCTGACGCTGGTGTGCCTGGCC
GGCCTGCTCATGCTGCTCACCGTGTTCGGCAACGTGCTCGTCATCATCGCCGTGTTCACG
AGCCGCGCGCTCAAGGCGCCCCAAAACCTCTTCCTGGTGTCTCTGGCCTCGGCCGACATC
CTGGTGGCCACGCTCGTCATCCCTTTCTCGCTGGCCAACGAGGTCATGGGCTACTGGTAC
TTCGGCAAGGCTTGGTGCGAGATCTACCTGGCGCTCGACGTGCTCTTCTGCACGTCGTCC
ATCGTGCACCTGTGCGCCATCAGCCTGGACCGCTACTGGTCCATCACACAGGCCATCGAG
TACAACCTGAAGCGCACGCCGCGCCGCATCAAGGCCATCATCATCACCGTGTGGGTCATC
TCGGCCGTCATCTCCTTCCCGCCGCTCATCTCCATCGAGAAGAAGGGCGGCGGCGGCGGC
CCGCAGCCGGCCGAGCCGCGCTGCGAGATCAACGACCAGAAGTGGTACGTCATCTCGTCG
TGCATCGGCTCCTTCTTCGCTCCCTGCCTCATCATGATCCTGGTCTACGTGCGCATCTAC
CAGATCGCCAAGCGTCGCACCCGCGTGCCACCCAGCCGCCGGGGTCCGGACGCCGTCGCC
GCGCCGCCGGGGGGCACCGAGCGCAGGCCCAACGGTCTGGGCCCCGAGCGCAGCGCGGGC
CCGGGGGGCGCAGAGGCCGAACCGCTGCCCACCCAGCTCAACGGCGCCCCTGGCGAGCCC
GCGCCGGCCGGGCCGCGCGACACCGACGCGCTGGACCTGGAGGAGAGCTCGTCTTCCGAC
CACGCCGAGCGGCCTCCAGGGCCCCGCAGACCCGAGCGCGGTCCCCGGGGCAAAGGCAAG
GCCCGAGCGAGCCAGGTGAAGCCGGGCGACAGCCTGCGCGGCGCGGGCCGGGGGCGACGG
GGATCGGGACGCCGGCTGCAGGGCCGGGGGAGGAGCGCGTCGGGGCTGCCAAGGCGTCGC
GCTGGCGCGGGCGGGCAGAACCGCGAGAAGCGCTTCACGTTCGTGCTGGCCGTGGTCATC
GGAGTGTTCGTGGTGTGCTGGTTCCCCTTCTTCTTCACCTACACGCTCACGGCCGTCGGG
TGCTCCGTGCCACGCACGCTCTTCAAATTCTTCTTCTGGTTCGGCTACTGCAACAGCTCG
TTGAACCCGGTCATCTACACCATCTTCAACCACGATTTCCGCCGCGCCTTCAAGAAGATC
CTCTGTCGGGGGGACAGGAAGCGGATCGTGTGA
|
| Target 1 GenBank Gene ID |
|
| Target 1 GeneCard ID |
ADRA2A  |
| Target 1 GenAtlas ID |
ADRA2A  |
| Target 1 HGNC ID |
HGNC:281  |
| Target 1 Chromosome Location |
10 |
| Target 1 Locus |
10q24-q26 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- Chung DA, Zuiderweg ER, Fowler CB, Soyer OS, Mosberg HI, Neubig RR: NMR structure of the second intracellular loop of the alpha 2A adrenergic receptor: evidence for a novel cytoplasmic helix. Biochemistry. 2002 Mar 19;41(11):3596-604. [PubMed
]
- Suryanarayana S, Daunt DA, Von Zastrow M, Kobilka BK: A point mutation in the seventh hydrophobic domain of the alpha 2 adrenergic receptor increases its affinity for a family of beta receptor antagonists. J Biol Chem. 1991 Aug 15;266(23):15488-92. [PubMed
]
- Wang CD, Buck MA, Fraser CM: Site-directed mutagenesis of alpha 2A-adrenergic receptors: identification of amino acids involved in ligand binding and receptor activation by agonists. Mol Pharmacol. 1991 Aug;40(2):168-79. [PubMed
]
- Chhajlani V, Rangel N, Uhlen S, Wikberg JE: Identification of an additional gene belonging to the alpha 2 adrenergic receptor family in the human genome by PCR. FEBS Lett. 1991 Mar 25;280(2):241-4. [PubMed
]
- Guyer CA, Horstman DA, Wilson AL, Clark JD, Cragoe EJ Jr, Limbird LE: Cloning, sequencing, and expression of the gene encoding the porcine alpha 2-adrenergic receptor. Allosteric modulation by Na+, H+, and amiloride analogs. J Biol Chem. 1990 Oct 5;265(28):17307-17. [PubMed
]
- Fraser CM, Arakawa S, McCombie WR, Venter JC: Cloning, sequence analysis, and permanent expression of a human alpha 2-adrenergic receptor in Chinese hamster ovary cells. Evidence for independent pathways of receptor coupling to adenylate cyclase attenuation and activation. J Biol Chem. 1989 Jul 15;264(20):11754-61. [PubMed
]
- Kobilka BK, Matsui H, Kobilka TS, Yang-Feng TL, Francke U, Caron MG, Lefkowitz RJ, Regan JW: Cloning, sequencing, and expression of the gene coding for the human platelet alpha 2-adrenergic receptor. Science. 1987 Oct 30;238(4827):650-6. [PubMed
]
|
| Target 1 Drug References |
- Brink CB, Wade SM, Neubig RR: Agonist-directed trafficking of porcine alpha(2A)-adrenergic receptor signaling in Chinese hamster ovary cells: l-isoproterenol selectively activates G(s). J Pharmacol Exp Ther. 2000 Aug;294(2):539-47. [PubMed
]
- Galeotti N, Bartolini A, Ghelardini C: Alpha-2 agonist-induced memory impairment is mediated by the alpha-2A-adrenoceptor subtype. Behav Brain Res. 2004 Aug 31;153(2):409-17. [PubMed
]
- Bockman CS, Jeffries WB, Abel PW: Binding and functional characterization of alpha-2 adrenergic receptor subtypes on pig vascular endothelium. J Pharmacol Exp Ther. 1993 Dec;267(3):1126-33. [PubMed
]
- Piletz JE, Sletten K: Nonadrenergic imidazoline binding sites on human platelets. J Pharmacol Exp Ther. 1993 Dec;267(3):1493-502. [PubMed
]
- Bockman CS, Gonzalez-Cabrera I, Abel PW: Alpha-2 adrenoceptor subtype causing nitric oxide-mediated vascular relaxation in rats. J Pharmacol Exp Ther. 1996 Sep;278(3):1235-43. [PubMed
]
|