TETRAHYDROZOLINE PHOSPHATE

US Approved OTC

First approved in 1954

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H16N2.H3O4P
Molecular Weight	298.2747
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.C1CN=C(N1)C2CCCC3=CC=CC=C23

InChI

InChIKey=HPGQQPUQEIRXHP-UHFFFAOYSA-N

InChI=1S/C13H16N2.H3O4P/c1-2-6-11-10(4-1)5-3-7-12(11)13-14-8-9-15-13;1-5(2,3)4/h1-2,4,6,12H,3,5,7-9H2,(H,14,15);(H3,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula	H3O4P
Molecular Weight	97.9952
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C13H16N2
Molecular Weight	200.2795
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.rxresource.org/prescription-information/Tyzine-Pediatric-Fougera-Pharmaceuticals-Inc.html

Tetrahydrozoline is an alpha adrenergic receptor agonist, which is used in form of nasal solution or spray (Tyzin) for decongestion of nasal and nasopharyngeal mucosa.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: www.ncbi.nlm.nih.gov/pubmed/18259967	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nasal congestion 26 Sources: http://www.rxresource.org/prescription-information/Tyzine-Pediatric-Fougera-Pharmaceuticals-Inc.html	Curative		Approved 8429	TYZINE Approved Use Tyzine Nasal Solution is indicated for decongestion of nasal and nasopharyngeal mucosa. Launch Date 1979

C_max

Value	Dose	Co-administered	Analyte	Population
0.218 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21972870/	2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		TETRAHYDROZOLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3.46 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21972870/	2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		TETRAHYDROZOLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21972870/	2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		TETRAHYDROZOLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
7500 ug single, oral Overdose Dose: 7500 ug Route: oral Route: single Dose: 7500 ug Sources: https://pubmed.ncbi.nlm.nih.gov/15388224	healthy, 16 years n = 1 Health Status: healthy Age Group: 16 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15388224	Other AEs: Sinoatrial node dysfunction... Other AEs: Sinoatrial node dysfunction (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15388224
0.3 mg/kg single, oral Overdose Dose: 0.3 mg/kg Route: oral Route: single Dose: 0.3 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21740144	healthy, 20 months-2 years n = 2 Health Status: healthy Age Group: 20 months-2 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/21740144	Other AEs: Bradycardia, Hypertension... Other AEs: Bradycardia (2 patients) Hypertension (1 patient) Gasping (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/21740144
250 ug 3 times / day multiple, oral Overdose Dose: 250 ug, 3 times / day Route: oral Route: multiple Dose: 250 ug, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20723124	unhealthy, 25 days n = 1 Health Status: unhealthy Age Group: 25 days Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20723124	Other AEs: Hypotonia... Other AEs: Hypotonia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20723124
250 ug 3 times / day multiple, oral Overdose Dose: 250 ug, 3 times / day Route: oral Route: multiple Dose: 250 ug, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20723124	unhealthy, 25 days n = 1 Health Status: unhealthy Condition: mild fever Age Group: 25 days Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20723124	Other AEs: Apnea... Other AEs: Apnea (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20723124
15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	Other AEs: Hypothermia, Bradycardia... Other AEs: Hypothermia (1 patient) Bradycardia (1 patient) Hypotension (1 patient) Miosis (1 patient) Lethargy (1 patient) Mucous membrane disorder (NOS) (1 patient) Bowel sounds decreased (1 patient) Chest pain (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8530784

AEs

AE	Significance	Dose	Population
Sinoatrial node dysfunction	1 patient	7500 ug single, oral Overdose Dose: 7500 ug Route: oral Route: single Dose: 7500 ug Sources: https://pubmed.ncbi.nlm.nih.gov/15388224	healthy, 16 years n = 1 Health Status: healthy Age Group: 16 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15388224
Hypertension	1 patient	0.3 mg/kg single, oral Overdose Dose: 0.3 mg/kg Route: oral Route: single Dose: 0.3 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21740144	healthy, 20 months-2 years n = 2 Health Status: healthy Age Group: 20 months-2 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/21740144
Bradycardia	2 patients	0.3 mg/kg single, oral Overdose Dose: 0.3 mg/kg Route: oral Route: single Dose: 0.3 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21740144	healthy, 20 months-2 years n = 2 Health Status: healthy Age Group: 20 months-2 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/21740144
Gasping	2 patients	0.3 mg/kg single, oral Overdose Dose: 0.3 mg/kg Route: oral Route: single Dose: 0.3 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21740144	healthy, 20 months-2 years n = 2 Health Status: healthy Age Group: 20 months-2 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/21740144
Hypotonia	1 patient	250 ug 3 times / day multiple, oral Overdose Dose: 250 ug, 3 times / day Route: oral Route: multiple Dose: 250 ug, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20723124	unhealthy, 25 days n = 1 Health Status: unhealthy Age Group: 25 days Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20723124
Apnea	1 patient	250 ug 3 times / day multiple, oral Overdose Dose: 250 ug, 3 times / day Route: oral Route: multiple Dose: 250 ug, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20723124	unhealthy, 25 days n = 1 Health Status: unhealthy Condition: mild fever Age Group: 25 days Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20723124
Bowel sounds decreased	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Bradycardia	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Chest pain	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Hypotension	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Hypothermia	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Lethargy	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Miosis	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784
Mucous membrane disorder (NOS)	1 patient	15000 ug single, oral Overdose Dose: 15000 ug Route: oral Route: single Dose: 15000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8530784	healthy, 41 years n = 1 Health Status: healthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8530784

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY573823	https://www.001chemical.com/chem/84-22-0
3B Scientific (Wuhan) Corp	3B2-4921	http://www.3bsc.com/index/pro_info.php?id=79861
AHH Chemical co.,ltd	MR-1085668	http://www.ahhchemical.com/product/MR-1085668.html
Alinda	ALBB-023224	http://alinda.ru/finechem_en_.html?i=ALBB-023224
Ambeed	A187603	https://www.ambeed.com/products/84-22-0.html
BLD Pharm	BD153519	http://www.bldpharm.com/products/84-22-0.html
Chem Scene	CS-0009512	http://www.chemscene.com/84-22-0.html
ChemMol	49416873	http://www.chemmol.com/chemmol/49416873.html
Chemspace	CSSB00011301665	https://chem-space.com/CSSB00011301665
Finetech	FT-0690208	http://www.finetechnology-ind.com/prod/detail/pub/84-22-0.html
Hairui	HR145170	http://www.hairuichem.com/en/product/84-22-0.html
MedChem Express	HY-B0556	https://www.medchemexpress.com/tetrahydrozoline.html
Molcore	MC573823	https://www.molcore.com/product/84-22-0
OChem	11845	http://www.ocheminc.com/index.php?act=psearch&pid=084T220
Oakwood	373421	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=144909&ExtHyperLink=1
Smolecule	S569467	https://www.smolecule.com/products/s569467
THE BioTek	bt-291936	https://www.thebiotek.com/product/others/bt-291936
Vitas-M Laboratory	STL163582	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL163582&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
eNovation Chemicals	D395049	https://www.enovationchem.com/ProductDetails.asp?ProductID=D395049
eNovation Chemicals	D767292	https://www.enovationchem.com/ProductDetails.asp?ProductID=D767292
iChemical	EBD53541	http://www.ichemical.com/chemicals/cas-84-22-0
mcule	MCULE-1878887684	https://mcule.com/MCULE-1878887684/

PubMed

Title	Date	PubMed
Viability of fibroblasts in cell culture after treatment with different chemical retraction agents.	2002 Jan	11844038
Pediatric Visine (tetrahydrozoline) ingestion: case report and review of imidazoline toxicity.	2003 Aug	12882493
[The tolerability of nasal drugs with special regard to preservatives and physico-chemical parameters].	2003 Nov	14634896
Sinoatrial node arrest following tetrahydrozoline ingestion.	2004 Oct	15388224
[Systemic involvement in premature infants after intranasal administration of tetryzoline drops].	2005 Oct	16219260
Simple HPLC determination of benzalkonium chloride in ophthalmic formulations containing antazoline and tetrahydrozoline.	2005 Sep-Oct	16316068
Antagonism by imidazoline-type drugs of muscarinic and other receptors in the guinea-pig ileum.	2006 Jul	16879492
Comparative evaluation of antimicrobial efficacy of sodium hypochlorite, MTAD, and Tetraclean against Enterococcus faecalis biofilm.	2007 Jul	17804328
Drug facilitated sexual assault using an over-the-counter ocular solution containing tetrahydrozoline (Visine).	2007 Jul	17320456
Prolonged cardiovascular effects after unintentional ingestion of tetrahydrozoline.	2008 Feb	18259967
Determination of tetrahydrozoline in urine and blood using gas chromatography-mass spectrometry (GC-MS).	2010	20077102
2-(1,2,3,4-Tetra-hydro-1-naphth-yl)imidazolium chloride monohydrate.	2010 Aug 18	21588668
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Tetrahydrozoline (Visine®) concentrations in serum and urine during therapeutic ocular dosing: a necessary first step in determining an overdose.	2011 Nov	21972870

Patents

Sample Use Guides

In Vivo Use Guide

Adults and Children 6 Years and Over, Tyzine 0.1% Nasal Solution: It is recommended that 2 to 4 drops be instilled in each nostril as needed, never more often than every three hours. Adults and Children 6 Years and Over, Tyzine 0.1% Nasal Spray: It is recommended to squeeze quickly and firmly three or four times the spray in each nostril as needed, never more often than every three hours. Children 2 to 6 Years of Age, Tyzine 0.05 % Pediatric Nasal Drops: It is recommended that 2 to 3 drops be instilled in each nostril as needed, and never more often than every three hours.

Route of Administration: Nasal

In Vitro Use Guide

Rat and rabbit aortae were treated with tetrahydrozoline at concentrations from 10(-7) to 10(-5) M to determine the drug relative efficacy. Emax value was 0.51 for the rabbit aortae and 0 for the rat aortae.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:01:16 GMT 2023` Edited by `admin` on `Sat Dec 16 10:01:16 GMT 2023`
Record UNII	79V49ERS3O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAHYDROZOLINE PHOSPHATE

Common Name

English

Tetryzoline phosphate [WHO-DD]

Common Name

English

TETRYZOLINE PHOSPHATE

Common Name

English

1H-IMIDAZOLE, 4,5-DIHYDRO-2-(1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL)-, PHOSPHATE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

94133-85-4