Compound: Proflavine
SMILES: n1c2c(cc3c1cc(N)cc3)ccc(c2)N
InChIKey: WDVSHHCDHLJJJR-UHFFFAOYSA-N
Synonyms: Proflavine, acridine-3,6-diamine, 92-62-6, Proflavin, 3,6-ACRIDINEDIAMINE, 3,6-Diaminoacridine, Isoflav base, Proflavina, Proflavinum, 2,8-Diaminoacridinium, 2,8-Diaminoacridine, 3,6-Diaminoacridinium, Diaminoacridine, CY3RNB3K4T, CHEBI:8452, DTXSID9043776, 3,6 diaminoacridine, 3,6-diamino acridine, 3,6 Diamino Acridine, Acridine, 3,6-Diamino, RefChem:176158, DTXCID7023776, 202-172-4, Proflavine [INN], Acridine, 3,6-diamino-, 3,7-Diamino-5-azaanthracene, MFCD00005030, Proflavine (hemisulfate), Profura, Progarmed, Proflavinum [INN-Latin], PRL, Proflavina [INN-Spanish], Proflavin hemisulfate;3,6-Diaminoacridine hemisulfate, 2,8-Diaminoacridine (European), CCRIS 1244, HSDB 7071, NCGC00166245-01, EINECS 202-172-4, UNII-CY3RNB3K4T, BRN 0166050, AI3-52128, 1bcu, 1qvt, 1qvu, 3,6-Acridinediamine hydrochloride, 3,6-diaminoacridin, proflavine-hemisulfate, PROFLAVINE [MI], PROFLAVINE [HSDB], PROFLAVINE [VANDF], NCIMech_000209, PROFLAVINE [WHO-DD], SCHEMBL27386, 5-22-11-00322 (Beilstein Handbook Reference), AE-562/12222295, CHEMBL55400, orb1305945, Proflavine;3,6-Diaminoacridine, SCHEMBL8149677, SCHEMBL29236615, SCHEMBL29600097, BDBM12590, WDVSHHCDHLJJJR-UHFFFAOYSA-, 2v57, HMS5085B07, AAA53173, ALBB-024962, HY-B1741, EBC-26205, SBB072167, STK380650, AKOS005449844, AT13412, CCG-339542, DB01123, NCGC00166245-02, DA-77083, NCI60_004643, NCI60_004767, NCI60_032077, ST012247, TS-08258, A3219, CS-0013756, NS00008797, S5776, AB00375967-03, AB00375967_04, (6-aminoacridin-3-yl)amine;sulfuric acid;hydrate, F600890, Q420454, SR-01000883943, SR-01000883943-1, BRD-K68408467-065-01-8, InChI=1/C13H11N3/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10/h1-7H,14-15H2
Theoretical properties:
molecular_formula: C13H11N3
molecular_weight: 209.25 g/mol
exact_mass: 209.095297364 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 16
topological_polar_surface_area: 64.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Yellow needles from alcohol. Solutions are brownish and when diluted are fluorescent.
color: Yellow needles from alcohol. Solutions are brownish and when diluted are fluorescent.
vapor_pressure: 0.00000009 [mmHg]
Descriptions:
{"pubchem": "3,6-diaminoacridine is an aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of burns and infected wounds. It has a role as a chromophore, an intercalator, an antibacterial agent, an antiseptic drug and a carcinogenic agent. It is a conjugate base of a 3,6-diaminoacridine(1+).", "chebi": "An aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of burns and infected wounds.", "chembl": "PROFLAVINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Proflavine, also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria. It has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic.\nProflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair-insertions and not substitutions. In the presence of light, proflavine can induce double-stranded breaks in DNA.\nProflavine is a fluorescent dye that is sometimes used in microscopic in-vivo imaging due to its intercalation properties. However, there was concern that women exposed to proflavin could develop cervical cancer since they have mutagenesis potential. However, the retrospective analysis performed by Pantano et. al. demonstrated that there is no increased cervical cancer risk after exposure to proflavine.\nIn astronomical spectroscopy proflavine present in interstellar clouds (derived from the modification in meteorites of polycyclic aromatic hydrocarbons by heteroatoms) strongly absorbs in the blue region at 445 nm. This makes difficult the recording of the spectra of stars that lie behind the clouds."}