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6-Aminohexanoic Acid

HCID 564
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1319-82-0
표준 SMILES
NCCCCCC(=O)O
InChIKey
SLXKOJJOQWFEFD-UHFFFAOYSA-N
분자식
C6H13NO2
평균 분자량
131.17 g/mol
단동위원소 질량
131.09462866

개요

6-aminohexanoic acid is an -amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator. It has a role as a metabolite, an antifibrinolytic drug and a hematologic agent. It is an epsilon-amino acid and an omega-amino fatty acid. It is functionally related to a hexanoic acid. It is a conjugate acid of a 6-aminohexanoate. It is a tautomer of a 6-aminohexanoic acid zwitterion.

이름 및 식별자

우선 이름
6-Aminohexanoic Acid
IUPAC
6-aminohexanoic acid
영어명
Aminocaproic Acid
분자식
C6H13NO2
분자량
0

이름 및 동의어

6-aminohexanoic acid6-Aminocaproic acidaminocaproic acid60-32-2Hexanoic acid, 6-amino-AcepramineEpsicapronEpsilcapraminCapramolCaprolisinAcepraminHemopar
이름 더 보기
Aminohexanoic acidAcido aminocaproicoAcidum aminocaproicumHexanoic acid, amino-Aminohexanoic acid USP/EP/BPAcidum aminocaproicum [inn-latin]Acido aminocaproico [inn-spanish]Acide aminocaproique [inn-french]
IpsilonRespraminAmikarEACAAminokapronAfibrinCaplaminAtsemin

데이터베이스 식별자

CAS
1319-82-0、60-32-2
PubChem CID
564
DTXSID
DTXSID0020070
ChEMBL
CHEMBL1046
ChEBI
CHEBI:16586
UNII
U6F3787206
EC Number

물성

구조 계산 물성보충 중

XLogP
-3
극성 표면적
63.3 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
5
무거운 원자 수
9
형식 전하
0
복잡도
83.1

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]
LogP-2.95
OdorODORLESS, OR NEARLY SO
TasteTASTELESS
Color/Form · 2건

FINE, WHITE, CRYSTALLINE POWDER

LEAVES FROM ETHER

Solubility · 3건

1 G IN 3 ML OF WATER; SLIGHTLY SOL IN ALCOHOL; PRACTICALLY INSOL IN CHLOROFORM & ETHER

505.0 mg/mL at 25 °C

0.9 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 2건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 78.6% (206 of 262) of all reports.

Warning

H315 (20.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 262 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 4건

Chemical: Hexanoic acid, 6-amino-

Hexanoic acid, 6-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanoic acid, 6-amino- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22890

Hexanoic acid, 6-amino-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Hexanoic acid, 6-amino-: Environment tier I assessment
Hazards Summary · 1건

Possible side effects in long-term therapy greater than 2 weeks include seizures, myopathy, renal failure, and kidney failure; [HSDB] May cause irritation; Effects in high-dose animal studies include convulsions or effect on seizure threshold and changes in the renal tubules; [MSDSonline] Not teratogenic in rabbits; [REPROTOX]

Special Reports · 1건

REVIEW: A PROFILE OF THE PHARMACOLOGY, THERAPEUTIC INDICATIONS, THE PREPARATIONS AND STRENGTHS AVAILABLE, THE DOSAGE, CONTRAINDICATIONS, TOXICITY, INTERACTIONS, PHARMACOKINETICS AND OTHER PHYSICAL PROPERTIES OF EPSILON-AMINOCAPROIC ACID.[PROFILE ON EPSILON AMINOCAPROIC ACID; AUST J PHARM 62(JUN) 403 (1981)]

화학 및 산업

약리 정보

ATC CodeB - Blood and blood forming organs
Pharmacodynamics · 1건

Aminocaproic acid works as an antifibrinolytic. It is a derivative of the amino acid lysine. The fibrinolysis-inhibitory effects of aminocaproic acid appear to be exerted principally via inhibition of plasminogen activators and to a lesser degree through antiplasmin activity. Aminocaproic acid may be a possible prophylactic for vascular disease, as it may prevent formation of lipoprotein (a), a risk factor for vascular disease.

Mechanism of Action · 3건

Aminocaproic acid binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin. With NO activation of plasmin, there is a reduction in fibrinolysis. This consequently will reduce the amount of bleeding post surgery. Elevated plasma levels of lipoprotein(a) have been shown to increase the risk of vascular disease. Lipoprotein 9a)a has two components, apolipoprotein B-100, linked to apolipoprotein (a). Aminocaproic acid may change the conformation of apoliprotein (a), changing its binding properties and potentially preventing the formation of lipoprotein (a).

A COMPETITIVE INHIBITOR OF ACTIVATORS OF PROFIBRINOLYSIN &, TO LESSER EXTENT, OF FIBRINOLYSIN. AS A CONSEQUENCE, IT SUPPRESSES FORMATION OF FIBRINOLYSIN, AN ENZYME WHICH DESTROYS FIBRINOGEN, FIBRIN, & OTHER CLOTTING COMPONENTS.

MICROCALORIMETRY AND UV AND IR SPECTROSCOPY WERE USED TO STUDY THE INTERMOLECULAR INTERACTIONS OF PLASMINOGEN AND PLASMIN WITH EPSILON-AMINOCAPROIC ACID (I) TO DETERMINE THE MECHANISM OF FIBRINOLYSIS INHIBITION. AT LOW DOSES, THE INHIBITORY EFFECT WAS DUE MAINLY TO BLOCKADE OF THE STAGE OF ACTIVATION OF PLASMINOGEN, WHEREAS THE EFFECTIVENESS OF HIGH CONCENTRATIONS OF I WAS ACHIEVED ALSO BY INACTIVATION OF THE ENZYMIC ACTIVITY OF PLASMIN.

Biological Half-LifeThe terminal elimination half-life is approximately 2 hours.
Metabolism/MetabolitesSixty-five percent of the dose is recovered in the urine as unchanged drug and 11% of the dose appears as the metabolite adipic acid.
FDA Pharmacological Classification

관련 반응

228건
반응 기록 만들기
HRID 7207 반응식
HRID 7207생성물로uspto-grants-2006_08
HRID 11905 반응식
HRID 11905반응물로uspto-grants-2006_08
HRID 14366 반응식
HRID 14366반응물로uspto-grants-2010_06
HRID 20904 반응식
HRID 20904반응물로uspto-grants-2010_06
HRID 35797 반응식
HRID 35797반응물로uspto-grants-1995_05
HRID 60413 반응식
HRID 60413반응물로uspto-grants-2016_09
HRID 78681 반응식
HRID 78681생성물로uspto-grants-2014_09
HRID 116949 반응식
HRID 116949반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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200-469-3
Nikkaji
J1.398F
· 2건

202-203 °C

205 °C

Physical Description · 3건

Wet Solid

White solid; [HSDB] White crystalline solid; [MSDSonline]

Solid

물리화학적 성질

녹는점
205 · 205-207 °C
Hazard Classes and CategoriesSkin Irrit. 2 (20.6%)

독성 정보

InteractionsPLASMINOGEN ACTIVATORS SUCH AS STREPTOKINASE & UROKINASE ARE USED TO TREAT THROMBOEMBOLIC DISORDERS. ...AMINOCAPROIC ACID COUNTERACTS THE THROMBOLYTIC EFFECT OF THESE DRUGS...
Adverse Effects · 2건

Neurotoxin - Other CNS neurotoxin

Although aminocaproic acid is generally well tolerated in patients, reported adverse effects of the drug include malaise, myalgias, renal impairment, seizures, hypotension, bradycardia, thrombosis, edemas, and injection site reactions. Less frequently, aminocaproic acid may also lead to gastrointestinal symptoms, such as nausea and diarrhea. In addition, there have been reports of nasal congestion and conjunctival suffusion with the usage of aminocaproic acid.

Toxicity Summary · 1건

Aminocaproic acid is associated with a low acute toxicity risk. Research on teratogenic in vitro studies has revealed no fetal abnormalities when administering aminocaproic acid dosages up to 5000 mcg/kg/d. Retinal changes have been reported in dogs after receiving aminocaproic acid orally over 1 year at doses approximately 7 times higher than the maximum recommended dose for in vivo use. A significant concern regarding aminocaproic acid treatment is whether this drug can increase patients' risk of thrombosis and intravascular coagulation. Although there are isolated reports of arterial or venous thrombosis, it is noteworthy that the underlying thrombotic comorbidity is present in each reported case.

Human Toxicity Excerpts · 3건

CARDIAC & HEPATIC NECROSES WERE FOUND @ POSTMORTEM EXAMINATION IN ONE PT WHO HAD RECEIVED THERAPEUTIC DOSES OF THE DRUG.

AMINOCAPROIC ACID MAY CAUSE ITCHING, ERYTHEMA, SKIN RASH, DIURESIS, HEARTBURN, NAUSEA, & DIARRHEA. ...HAS ANTIADRENERGIC EFFECT SIMILAR TO GUANETHIDINE, SO THAT NASAL STUFFINESS, CONJUNCTIVAL SUFFUSION, & HYPOTENSION MAY OCCUR. ...MAY ENHANCE THROMBOTIC PROCESSES BY SUPPRESSION OF REACTIVE FIBRINOLYSIS...

AMICAR HAS BEEN USED IN SUBARACHNOID HEMORRHAGE TO PROMOTE CLOTTING, BUT CEREBRAL THROMBOSIS HAS BEEN REPORTED IN VARIOUS VASCULAR COMPARTMENTS FOLLOWING ITS USE. TWO PATIENTS ARE DESCRIBED WHO HAD CEREBRAL ANGIOGRAPHY AFTER AMICAR THERAPY WHICH DEMONSTRATED THROMBOSIS UNRELATED TO VASCULAR SPASM OR TO TECHNICAL COMPLICATIONS OF ANGIOGRAPHY.

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Aminocaproic acid

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 3건

/AMINOCAPROIC ACID/...IS TERATOGENIC IN ANIMALS...

SUBENDOCARDIAL HEMORRHAGES & MYOCARDIAL DEPRESSION HAVE BEEN ASSOCIATED WITH ADMIN OF AMINOCAPROIC ACID IN SEVERAL ANIMAL SPECIES. DRUG MAY TRANSIENTLY ALTER PROTEIN METABOLISM BY INHIBITING UTILIZATION OF LYSINE.

...WHEN GIVEN IV TO CATS HAS SYMPATHOMIMETIC EFFECTS, INCL DILATED PUPILS & EXOPHTHALMOS ATTRIBUTABLE PARTLY TO RELEASE OF CATECHOLAMINES. ...CHRONICALLY BY MOUTH IT OCCASIONALLY CAUSES NASAL CONGESTION & CONJUNCTIVAL HYPEREMIA.

· 6건

U6F3787206

AMINOCAPROIC ACID

Established Pharmacologic Class [EPC] - Antifibrinolytic Agent

Physiologic Effects [PE] - Decreased Fibrinolysis

Aminocaproic acid is an Antifibrinolytic Agent. The physiologic effect of aminocaproic acid is by means of Decreased Fibrinolysis.

AMINOCAPROIC ACID

MeSH Pharmacological ClassificationAgents that prevent fibrinolysis or lysis of a blood clot or thrombus. Several endogenous antiplasmins are known. The drugs are used to control massive hemorrhage and in other coagulation disorders.
Absorption, Distribution and Excretion · 5건

Absorbed rapidly following oral administration. In adults, oral absorption appears to be a zero-order process with an absorption rate of 5.2 g/hr. The mean lag time in absorption is 10 minutes. After a single oral dose of 5 g, absorption was complete (F=1).

Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.

23.1 ± 6.6 L

169 mL/min

AMINOCAPROIC ACID IS WELL ABSORBED ORALLY... THIS DRUG IS EXCRETED RAPIDLY IN URINE, LARGELY UNCHANGED, & PEAK PLASMA LEVELS ARE OBTAINED ABOUT 2 HR AFTER A SINGLE ORAL DOSE.

Tissue LocationsEpidermis
Cellular LocationsExtracellular
Metabolite PathwaysAminocaproic Acid Action Pathway

용도 및 제조

Uses · 4건

Used as a captive chemical intermediate in the production of nylon 6; [HSDB] Used as a hemostatic; [Merck Index] An inhibitor of fibrinolysis and sold as Amicar; [REPROTOX]

ANTIDOTE FOR OVERDOSAGE IN FIBRINOLYTIC THERAPY; CAPTIVE CHEM INT IN PRODUCTION OF NYLON 6

MEDICATION

MEDICATION (VET):

U.S. Exports · 2건

(1972) No Data

(1975) No Data

U.S. Imports · 2건

(1975) 3.8X10+6 GRAMS (PRINCPL CUSTMS DISTS)

(1976) 5.50X10+6 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3건

2023: 50,000 - <250,000 lb

(1974) GREATER THAN 4.54X10+5 GRAMS

(1975) No Data

Consumption PatternsEXCLUDING CAPTIVE USE IN NYLON 6 PRODUCTION FROM CAPROLACTAM, PROBABLY 100% IS USED AS A FIBRINOLYTIC INHIBITOR (1976)
Industry UsesOther
Methods of Manufacturing · 2건

HEATING OF AN AQUEOUS SOLUTION OF CAPROLACTAM WITH CALCIUM HYDROXIDE TO GIVE CALCIUM AMINOCAPROATE, FOLLOWED BY REACTION WITH SULFURIC ACID

...FROM EPSILON-BENZOYLAMINOCAPRONITRILE: RUZICKA, HUGOSON, HELV CHIM ACTA 4, 472 (1921); FROM EPSILON CAPROLACTAM...SULZBACHER, MFR CHEMIST 33, 463 (1963); FROM 1-HYDROXYCYCLOHEXYLHYDROPEROXIDE: MINISCI, PORTOLANI; GAZZ CHIM ITAL 89, 1941 (1959).

Formulations/Preparations...AVAILABLE AS INJECTION (250 MG/ML), SYRUP (250 MG/ML) & TABLETS (500 MG).
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
General Manufacturing Information · 2건

All Other Basic Organic Chemical Manufacturing

Hexanoic acid, 6-amino-: ACTIVE